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[ CAS No. 3411-95-8 ] {[proInfo.proName]}

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Chemical Structure| 3411-95-8
Chemical Structure| 3411-95-8
Structure of 3411-95-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 3411-95-8 ]

CAS No. :3411-95-8 MDL No. :MFCD00022869
Formula : C13H9NOS Boiling Point : -
Linear Structure Formula :- InChI Key :MVVGSPCXHRFDDR-UHFFFAOYSA-N
M.W : 227.28 Pubchem ID :18874
Synonyms :

Calculated chemistry of [ 3411-95-8 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 15
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 67.08
TPSA : 61.36 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -4.92 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.12
Log Po/w (XLOGP3) : 3.9
Log Po/w (WLOGP) : 3.67
Log Po/w (MLOGP) : 2.67
Log Po/w (SILICOS-IT) : 4.19
Consensus Log Po/w : 3.31

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -4.33
Solubility : 0.0105 mg/ml ; 0.0000464 mol/l
Class : Moderately soluble
Log S (Ali) : -4.89
Solubility : 0.00295 mg/ml ; 0.000013 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.92
Solubility : 0.00274 mg/ml ; 0.0000121 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.29

Safety of [ 3411-95-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 3411-95-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 3411-95-8 ]

[ 3411-95-8 ] Synthesis Path-Downstream   1~58

  • 1
  • [ 90-02-8 ]
  • [ 137-07-5 ]
  • [ 3411-95-8 ]
YieldReaction ConditionsOperation in experiment
98% With cadmium sulphide In methanol at 20℃; for 0.333333h; Irradiation; Catalytic procedure General procedure: In the experimental procedure for catalytic reaction, amixture of aldehyde (3 mmol), 2-aminothiophenol (3 mmol) and CdSnanosphere (5 mg) was taken in a 100 ml double walled quartz beaker flaskhaving water inlet and outlet to maintain the temperature of the reactionvessel at room temperature in methanol (20 ml). The beaker was exposed tovisible light under stirring condition for the required time period (Table 3).After completion of the reaction (monitored by TLC and GC), methanol wasevaporated by rotary and the product was dissolved in dichloromethane. Thecatalyst was separated from the reaction mixture by centrifugation.Dichloromethane was then evaporated to dryness and the product waspurified by column chromatography using silica gel G60.
98% With 3,6-di(2'-pyridyl)-1,2,4,5-tetrazine In ethanol at 20℃; for 0.5h; Irradiation; Green chemistry;
98% With manganese doped CdS nanoparticles In lithium hydroxide monohydrate at 90℃; for 1.5h; chemoselective reaction; 3.3. Catalyst activity measurement General procedure: In a 50 ml round bottom flask, o-phenylenediamine/aminothiophenol (1 mmol) and aromatic aldehydes (1 mmol) in water (4 ml) were mixed and stirred at 90°C. To this, catalyst was added. The progress of the reaction was checked on TLC. After completion, the reaction mixture was cooled at room temperature. Then, it was extracted with ethyl acetate; the organic layer was dried over sodium sulphate and concentrated in a vacuum to afford the crude products. The pure products were obtained by recrystallization from ethanol.
96% With aminosulfonic acid In lithium hydroxide monohydrate at 20℃; for 0.333333h; Green chemistry;
96% With hydrogenchloride; dihydrogen peroxide In methanol; lithium hydroxide monohydrate at 20℃; for 2h; 3 Method 2: 2-Aminothiophenol (250 mg, 2 mmol) and 2-hydroxybenzaldehyde (244 mg, 2 mmol) were dissolved in methanol (5 mL).Concentrated hydrochloric acid (37%, 169 μL) and hydrogen peroxide (30% aq, 188 μL) were added dropwise to the solution.Then react under air at room temperature for 2 h; until the reaction is finished, the reaction solution is filtered.The residue was washed with methanol and dried in vacuo to give a white solid.(435 mg, yield 96%) (ie Method 2-Compound IV-1).
95% for 0.166667h; microwave irradiation;
95% With CAN; dihydrogen peroxide at 50℃; for 0.266667h;
95% With iron (ΙΙΙ) nitrate nonahydrate; dihydrogen peroxide at 50℃; for 0.1h;
95% With nitric acid supported on a silica gel at 20℃; General procedure for the synthesis of 2-aryl/heteroaryl/styryl/alkylbenzothiazoles 3 General procedure: To a mixture of 2-aminothiophenol 1 (2.0 mmol) and aryl/heteroaryl/styryl/alkylaldehyde 2 (2.0 mmol) in a vial was added SiO2-HNO3 (2 wt% to the aldehyde)and shaken at room temperature. Instantly, an exothermic reaction occurred withcompletion of the reaction (TLC) and the reaction mixture became a yellowishorangesolid that was directly chromatographed over a silica gel column to affordpure 2-aryl/heteroaryl/styryl/alkylbenzothiazole 3 (Table 3).
95% With Amberlite IR-120 for 0.0833333h; Microwave irradiation; Green chemistry; General procedures for the synthesis of compounds 3a-l General procedure: Catalytic amount of Amberlite IR-120 resin was added to the equimolar (1:1) mixture of 2-aminothiophenol (1) and arylaldehyde (2a-l) in a microwave vassal. Then the reaction vassal was subjected to microwave oven for 5-10 min at 245 Watt. The progress of the reaction was monitored by TLC (3:1 hexane/ethyl acetate) and a change in colour of the solution was observed after the completion of the reaction. After complete conversion of starting materials into product; the resin was filtered off and the filtrate was evaporated to dryness in rotor evaporator. The crude product was further recrystallized from ethyl acetate in hexane (1:3). Yellow, orange or red needle like crystals were found with 90-95% yield.
93% With yttrium(III) chloride In ethanol for 0.5h; Reflux; Green chemistry; A general procedure for preparation of dihydropyrazines 3 General procedure: YCl3(0.0098 g, 0.05 mmol) were dissolved in 10mL EtOH and stirred until the soliddissolved completely in refluxing, then 2-aminobenzenethiols 1a (0.118 mL, 1.1mmol) and benzaldehyde 2a (0.101 ml, 1.0 mmol) was added into thereaction mixture. After 30min, TLC showed the reaction to be complete. Thereaction mixture was cooled to r.t., and then evaporated in vacuum. The productpurified by column chromatography (PE-EtOAc= 20:1) to give white solid 3a(0.2092 g, 99%)
92% With tungstophosphoric acid impregnated zirconium phosphate at 20℃; for 0.25h; Neat (no solvent);
92% In methanol for 12h;
92% With copper(II)-diaminosarcophagine-functionalized mesoporous silica (SBA-15) nanocatalyst In neat (no solvent) at 100℃; for 0.666667h; Green chemistry;
92% With disodium metabisulfite In N,N-dimethyl-formamide for 3h; Inert atmosphere; Reflux; 1.5 (5) Synthesis of Compound 2-1 Salicylaldehyde (961mg, 7.87mmol, 1eq) and Na2S2O5 (1.5mg, 7.87mmol, 1eq) was dissolved in 10mL DMF, and then added o-aminothiophenol (1.0g, 7.87mmol, 1eq), nitrogen, the reaction was heated at reflux for 2-3 hours, the reaction by TCL detection plate, after completion of the reaction, was cooled, poured into 200mL water, to produce solid, filtered under reduced pressure, and dried in vacuo to give the pure product. The yield was 92%.
91% With calcinated eggshell at 20℃; for 0.433333h; Green chemistry; General procedure for the preparation of 2-arylbenzothiazoles General procedure: A mixture of an appropriate aldehyde 1 (1 mmol), o-aminothiophenol 2 (1 mmol)and calcinized eggshell (0.050 g) were ground under solvent free conditions using mortar and pestle (Scheme 1). The progress of the reaction was monitored by thinlayer chromatography. After completion of the reaction, the solid product was dissolved in ethyl acetate, and the catalyst was separated by decantation and washed with hot ethanol. The product was obtained by evaporation of ethyl acetate. The products are recrystallized using ethanol, and their formations were confirmed by comparison of their physical and spectral data with the authentic samples from the literature. The separated catalyst was dried at 100 °C and reused for a similar reaction. The spectral data FT-IR, 1H-NMR, and MS of all synthesized compoundsare reported. The characterization data of some representative synthesizedcompounds are shown below.
90% With Sulfonated Porous Carbon In lithium hydroxide monohydrate for 0.116667h; Microwave irradiation;
90% With ferric hydrogen sulphate In ethanol for 0.5h; Reflux; chemoselective reaction;
90% With 15 wt% SnO2/SiO2 In ethanol; lithium hydroxide monohydrate for 1.16667h; Reflux;
90% With polymer-supported Nickel(II) Schiff base complex In lithium hydroxide monohydrate at 50℃; for 12h; Inert atmosphere;
90% With cadmium sulphide In methanol for 1h;
90% With air; epichlorohydrin cross-linked β-cyclodextrin polymer β-CDP In lithium hydroxide monohydrate at 60℃; for 3h; Green chemistry; 4.3. General procedure for the synthesis of 2-arylbenzothiazole General procedure: For a typical reaction run, o-aminothiophenol (1mmol, 125mg) was dissolved indeionised water (25 mL) at 60°C in a 100mL 3-necked round bottom flask fitted with a reflux condenser andmagnetic stirrer. β-CDP (1 g) was added to the vessel and the mixture was heated to 60°C in an oil bath with electric heater. Substituted aldehyde (1.2mmol) was added to the reaction system and it was stirred for 2 h at 60°C. The progress of the reactionwas monitored by TLC. When the reaction was finished, the mixture was extracted withethyl acetate and dried over anhydrous sodium sulfate. Then, ethyl acetate was removed in vacuum. All of the products are known compounds and characterized easily by comparison with melting point, IR and 1H NMR spectral data reported in literature.[53-56]
90% With Yb/MCM-41 molecular sieve In ethanol at 80℃; for 4h; 10 Example 10 Synthesis of 2- (2-hydroxyphenyl) benzothiazole A mixture of 2-aminothiophenol (1.1mmol), 2- hydroxybenzaldehyde (1 mmol of) and Yb / MCM-41 (0.01mmol) added to a round bottom flask was added 5ml of absolute ethanol, heated under reflux with stirring at 80 4h.Progress of the reaction is detected by TLC, the mixture was filtered after completion of the reaction, the resulting white Yb / MCM-41 molecular sieve catalyst, recycling, and the filtrate solvent was removed by rotary evaporation, and then separated by column chromatography to give the pure product, yield 90 %.
90% With silver(I) nitrate In dimethyl sulfoxide at 20℃;
90% With ruthenium silicate (Ru/Si, 1:100) zeolite In neat (no solvent) at 90℃; General procedure for synthesis of 2-arylbenzothiazoles General procedure: To the synthesis of 2-arylbenzothiazoles 3 (a-i) from a mixture of 2-aminothiophenol (0.001 mol), benzaldehydes (0.001 mol) and catalytic amount of (0.04 gm) RS-1 under solvent free conditions was refluxed at 90 °C for the prescribed time. The reaction progress was monitored by TLC (ethyl acetate: PET ether = 3:7 as eluent), after completion of the reaction, the product and catalyst were separated by simple filtration, and catalyst was easily separated from the reaction mixture. Finally, crude product obtained was crystallized from ethanol to afford desired pure product. The representative compound was characterized by FTIR 1H, 13C NMR and HRMS.
89% With ZnO-beta zeolite In ethanol for 1h; Reflux;
89% With H3PO4/TiO2-ZrO2(1/1)-cetyl pyridinium bromide at 20℃; for 0.416667h; General procedure: A mixture of 2-aminothiophenol (1 mmol, 0.995 g), aldehyde (1 mmol), and H3PO4-TiO2- ZrO2 (1/1) (40 mg, 30 wt%H3PO4) were added in a beaker and the reaction mixture was mixed properly with the help of glass rod under solvent-free condition at room temperature. The progress of the reaction was monitored by TLC (ethylacetate-hexane, 4:6). After completion of the reaction, the reaction mixture was dispersed in ethyl acetate (5 mL) and filtered and the catalyst was washed several times with ethyl acetate and acetone. Then, the filtrate was evaporated under reduced pressure to isolate a solid residue and recrystallized from hot ethanol (10 mL) to afford the corresponding products. All of the 2-arylbenzothiazole products were characterized by IR, 1H NMR, 13C NMR, and mass spectroscopy and identified by comparison of their physical and spectral data with those of authentic samples.[34,35]
89% With hydrogenchloride; dihydrogen peroxide In ethanol; lithium hydroxide monohydrate at 25℃; for 0.5h;
88% With hydrogenchloride; trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane In lithium hydroxide monohydrate; acetonitrile at 20℃; for 0.35h;
88% With hexamethylenetetramine-bromine complex In acetonitrile for 0.06h; Microwave irradiation;
88% With hydrogenchloride; dihydrogen peroxide In ethanol; lithium hydroxide monohydrate at 20℃; for 0.5h;
88% With copper(II)-diamine sarcophagine complex functionalized mesoporous silica SBA-15 In lithium hydroxide monohydrate for 0.333333h; Reflux;
88% With potassium carbonate; 3-butyl-1-methyl-1H-imidazol-3-ium iodide In o-dimethylbenzene; para-xylene; 1,3-dimethylbenzene at 120℃; for 10h; Green chemistry; General procedure A General procedure: Into a 15x150 mm glass tube were layered o-amino phenol (1a-1d)/benzenethiol (4) (1 mmol) and corresponding aldehyde (1 mmol), xylene (3 mL; mixture of o, m, p-xylene), 0.25 mmol K2CO3 (34 mg) and NHC precursor G (0.1 mmol, 26 mg), the mixture was lowered under pre-heated oil bath, the mixture was stirred vigorously for 10 hours under air atmosphere. After reaction, the mixture was diluted with ethyl acetate, filtrated, the organic solution was concentrated under vacuum, the residue was applied on silica gel column chromatography, which afforded the corresponding oxidative cyclization product 3aa-3dd; 5a-5n.
87% With nano silica-supported boron trifluoride (nano BF3/SiO2) In ethanol at 20℃; for 0.583333h; 4.2.2. General procedure for the synthesis of 2-arylbenzothiazoles catalyzed by nanoBF3/SiO2 General procedure: To a mixture of 2-aminothiophenol (1 mmol, 0.995 g) and aldehyde (1 mmol) in ethanol (10 ml), nano BF3/SiO2 (0.05 g, 25 mol% BF3) was added in a beaker and the reaction mixture was mixed properly with the help of a glass rod and stirred in ambient temperature for the time indicated in Table 3. The progress of the reaction was monitored by TLC (ethyl acetate:hexane, 6:4), after completion of the reaction the solvent was removed under reduced pressure, then the mixture was cooled and dichloromethane (15 ml) was added to the mixture and filtered to remove the catalyst. Then the filtrate was evaporated under reduced pressure to isolate a solid residue, and recrystallized from ethanol (10 ml) to afford the corresponding products and the catalyst residue was washed with acetone and reused. All of the 2-arylbenzothiazole products were identified by physical and spectroscopic data as follows.
87% With zinc(II) oxide In neat (no solvent) at 20℃; for 0.5h; Milling; Green chemistry;
87% With titanium tetra-n-butoxide In ethanol at 20℃;
87% With mesoporous Cu(II)-Glycerol-MCM-41 nanocatalyst In ethanol at 25℃; for 4.5h; 3.3. General procedure for the synthesis of benzothiazoles General procedure: In a 25-mL, round-bottom flask, a mixture of o-aminothiophenol(1.0 mmol), aldehyde (1.0 mmol) and Cu(II)-Glycerol-MCM-41(7 mg) in EtOH (3 mL) was stirred magnetically at room temperaturefor the appropriate time (Table 1). After completion of thereaction, as indicated by TLC, the reaction mixture was filtered toisolate the nanocatalyst and the crude product (filtrate) was purifiedby column chromatography on silica gel or recrystallization intoluene to give the desired products.
86% With toluene-4-sulfonic acid In PEG-200/400 for 0.0833333h; Microwave irradiation;
86% With nano titania supported sulfonic acid In neat (no solvent) at 70℃; for 0.333333h; Green chemistry; General Procedure for Preparation of Benzothiazole Derivatives General procedure: In a typical experiment, 2-aminothiophenole (1 mmol), aromatic aldehyde (1 mmol),and catalyst (0.099 mmol) in solvent free condition were taken in a 25-mL round-bottomedflask and was stirred at 70 C for an appropriate time. The reaction mixture was cooled,eluted with hot ethanol (5 mL) and was centrifuged and filtrated to collect the formedprecipitate. The crude product was recrystallized from ethanol to yield pure benzothiazolederivatives.
86% With uronium nitrate In neat (no solvent) at 20℃; for 0.0333333h; 4.3. Synthesis of benzothiazoles General procedure: 2-Aminothiophenol 1 (2.0 mmol) and carbaldehyde 2 (2.0 mmol) were mixed in a conical flask and NH2CONH2.HNO3 (1.5 wt % of aldehydes) was added to it. This mixture was shaken at room temperature. An instant exothermic reaction occurred with completion of reaction (TLC) and gave yellowish orange solid that was directly chromatographed over silica gel column to afford pure 2-aryl/heteroaryl/styryl/alkylbenzothiazole 3 (Table 3). The structures of synthesized compounds were confirmed by the overlapping 1H, 13C NMR and melting points data. The spectral data of some of the synthesised compounds are given below.
86% With C10H22N2(2+)*2HO4S(1-) In lithium hydroxide monohydrate for 0.666667h; Reflux; 2.6 General Procedure for Synthesis of 2-Phenylbenzothiazoles General procedure: A mixture of 2-aminothiophenol (1mmol) and aldehydes(1mmol) in water (5mL) was mixed and refluxed in the presence of DDAIL (DABCO based Dicationic Acidic IonicLiquid) (3mol%) for an appropriate time. The reaction mixture was cooled to room temperature after completion of the reaction (monitored by TLC) and extracted with ethyl acetate.The organic layer and aqueous layers were separated,the organic layer was concentrated under reduced pressure,and the crude product was purified by recrystallization with methanol.
85% With γ-Al2O3 at 120℃; for 0.5h;
85% Stage #1: o-hydroxybenzaldehyde; 2-amino-benzenethiol In 5,5-dimethyl-1,3-cyclohexadiene at 120℃; for 0.166667h; Stage #2: With 1,3-dimethyl-1H-imidazol-3-ium iodide; potassium carbonate In 5,5-dimethyl-1,3-cyclohexadiene for 12h; 14 Example 14, 2- (2-hydroxyphenyl) benzothiazole To 10 ml of a reaction tube was added 10 mmol of 1.25 g of 2-aminothiophenol and 10 mmol of 2-hydroxybenzaldehyde, 1.22 g of 30 ml of xylene were added and the mixture was stirred at 120 ° C for 10 minutes. After completion of the reaction by TLC, 1 mmol of imidazole (8) 224 mg, 2.5 mmol potassium carbonate (350 mg). After 12 hours of reaction, the solution was dried under reduced pressure. The resulting crude product was isolated by column chromatography to give the product to be more than 1.92 g and the yield was more than 85%.
85% With oxygen In neat (no solvent) at 20℃; for 0.666667h; General procedure for the preparation of 2-aryl/hete-roaryl benzothiazoles catalyzed by chitosan-SO3H In around bottom equipped flask 2-mercaptoaniline (1) (1 mmol), substituted aryl/heteroaryl aldehydes 2(a-o) (1 mmol) and CS-SO3H (2 mol %) is stirred at room temperature for 30 min in presence of oxygen balloon. The reaction was monitored by using TLC. Upon completion of the reaction, the reaction mass was quenched to absolute ethanol. The precipitated CS-SO3Hwas filtered and reused for subsequent reactions. The filterate was concentrated and obtained the curde product. Further thecrude product was recrystallized from ethanol and obtained pure products 3(a-o)
84% With 1,3,5-trichloro-2,4,6-triazine; oxygen In acetonitrile at 20℃; for 3.5h;
84% With cerium(IV) oxide In lithium hydroxide monohydrate at 20℃; for 0.333333h; General process for the synthesis of 2-substitutedbenzothiazole General procedure: Amixture of 2-aminothiophenol (1 mmol) and benzaldehyde (1 mmol) wasstirred in presence of Nano CeO2 (5 mol %) in water at roomtemperature for 20 minutes. After completion, the reaction mixture was dilutedwith ethyl acetate and subsequently centrifuged to get the catalyst. Further thereaction mixture was extracted with ethyl acetate (10 x 3mL) and dried over Na2SO4. The solvent was evaporated under reducedpressure to obtain product. The crude product was purified on silica gel columnby using pet ether and ethyl acetate as solvent to get the pure product
84% With iron(III) dodecyl sulfate In lithium hydroxide monohydrate at 60℃; for 0.133333h; Sonication; Green chemistry;
83% With air In ethyl acetate at 20℃; Irradiation; General Procedures: Preparation of the benzothiazole 3a General procedure: To a 20 mL glass tube with a stir bar was charged 2-aminothiophenol 1a (50 mg, 0.4 mmol), benzaldehyde 2a (51 mg, 0.48 mmol) and EtOAc (2 mL). The solution was stirred at room temperature with the irradiation of a 12 W blue LED for 6 h. The solvent was removed under vacuum. The residue was purified by column chromatography over silica gel (petroleum ether/ethyl acetate = 40/1) to give the product 3a (77 mg, 91%).
82% With trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane; hydrogen bromide In acetonitrile at 20℃; for 0.433333h;
82% In ethanol at 20℃; for 1h; Milling;

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[35]Sharma, Hemant; Singh, Narinder; Jang, Doo Ok [Green Chemistry, 2014, vol. 16, # 12, p. 4922 - 4930]
[36]Naeimi, Hossein; Heidarnezhad, Arash [Journal of the Chinese Chemical Society, 2014, vol. 61, # 9, p. 1004 - 1008]
[37]Noroozi Pesyan, Nader; Batmani, Hana; Havasi, Forugh [Polyhedron, 2019, vol. 158, p. 248 - 254]
[38]Location in patent: experimental part Deligeorgiev, Todor G.; Kaloyanova, Stefka; Vasilev, Aleksey; Vaquero, Juan J. [Phosphorus, Sulfur and Silicon and the Related Elements, 2010, vol. 185, # 11, p. 2292 - 2302]
[39]Amoozadeh, Ali; Azadeh, Rahmat Allah; Rahmani, Salman; Salehi, Mehdi; Kubicki, MacIej; Dutkiewicz, Grzegorz [Phosphorus, Sulfur and Silicon and the Related Elements, 2015, vol. 190, # 11, p. 1874 - 1883]
[40]Kumar, Parvin; Bhatia, Rimpy; Khanna, Radhika; Dalal, Aarti; Kumar, Dinesh; Surain, Parveen; Kamboj, Ramesh C. [Journal of Sulfur Chemistry, 2017, vol. 38, # 6, p. 585 - 596]
[41]Makone, Sangita; Pinate, Priyanka [Catalysis Letters, 2022]
[42]Ding, Mei-Fang; Chen, Chia-Pei; Lin, Shaw-Tao [Journal of the Chinese Chemical Society, 2013, vol. 60, # 6, p. 645 - 649]
[43]Current Patent Assignee: FUDAN UNIVERSITY - CN106674145, 2017, A Location in patent: Paragraph 0038; 0039
[44]Bathula, Surendra Bose; Khagga, Mukkanti; Venkatasubramanian, Hariharakrishnan [Asian Journal of Chemistry, 2018, vol. 30, # 7, p. 1512 - 1516]
[45]Location in patent: experimental part Maleki, Behrooz; Azarifar, Davood; Hojati, Seyede Fateme; Veisi, Hojat; Gholizadeh, Mostafa; Salehabadi, Hafezeh; Moghadam, Mona Khodaverdian [Journal of Heterocyclic Chemistry, 2011, vol. 48, # 2, p. 449 - 453]
[46]Shelkar, Radheshyam; Sarode, Sachin; Nagarkar, Jayashree [Tetrahedron Letters, 2013, vol. 54, # 51, p. 6986 - 6990]
[47]Pirbasti, Fateme Ghanbari; Mahmoodi, Nosrat Ollah [Journal of the Chinese Chemical Society, 2017, vol. 64, # 1, p. 80 - 86]
[48]Ye, Lin-miao; Chen, Jie; Mao, Peng; Mao, Zhi-feng; Zhang, Xue-jing; Yan, Ming [Tetrahedron Letters, 2017, vol. 58, # 9, p. 874 - 876]
[49]Location in patent: experimental part Khosravi, Kaveh; Kazemi, Samira [Journal of the Chinese Chemical Society, 2012, vol. 59, # 4, p. 557 - 560]
[50]Banerjee, Mainak; Chatterjee, Amrita; Kumar, Vikash; Bhutia, Zigmee T.; Khandare, Dipratn G.; Majik, Mahesh S.; Roy, Biswajit Gopal [RSC Advances, 2014, vol. 4, # 74, p. 39606 - 39611]
  • 2
  • [ 137-07-5 ]
  • [ 69-72-7 ]
  • [ 3411-95-8 ]
YieldReaction ConditionsOperation in experiment
92% Stage #1: 2-amino-benzenethiol; salicylic acid In toluene at 80℃; for 1h; Stage #2: With phosphorus trichloride In toluene at 40 - 100℃; for 6h;
92% Stage #1: 2-amino-benzenethiol; salicylic acid In toluene at 100℃; for 1h; Stage #2: With phosphorus trichloride In toluene at 40 - 60℃; for 6.5h; 1.2 Synthesis of 2- (2-hydroxyphenyl) benzothiazole (BTZ). Add 30mmol salicylic acid and 36mmol o-aminothiophenol to the three-necked flask in turn, add an appropriate amount of toluene,The reaction was stirred at ~ 100 ° C to complete dissolution for 1 h. Then reduce the temperature to 40 60 , and slowly drop 5mL of phosphorus trichloride within 0.5h.Add to the reaction system, stir at reflux until completely clear, and react for 6h. After the reaction is completed, the reaction solution is cooled to room temperature.A white solid was obtained and filtered to obtain BTZ white needle crystals with a yield of 92%.
85% With polyphosphoric acid at 180℃; for 3h;
82% With triphenyl phosphite; tetrabutylammomium bromide at 120℃; for 1h; 2. General procedure General procedure: A mixture of 1.55 g (5 mmol) of triphenyl phosphite (TPP), 1.66-2.25 g (5-7 mmol) of tetrabutylammonium bromide (TBAB), 0.625 g (5 mmol) of 2-aminothiophenol, and the corresponding substituted benzoic acid (5 mmol) in a 25 mL round bottomed flask was placed in an oil bath. The solution was stirred (15-60 minutes depending on the type of acid used) at 120oC. The product precipitated from the viscous solution by adding MeOH, and the resulting solid was filtered off and washed with cold MeOH to give the desired benzothiazole.
80% With methanesulfonic acid; silica gel at 140℃; for 4h;
65% With phosphorus trichloride In toluene for 4h; Heating;
40% With polyphosphoric acid at 180℃; for 5h; Inert atmosphere;
34.7% at 180℃; for 5h; Inert atmosphere; 2.2.1 2-(2-Hydroxyphenyl)benzothiazole (1) 1 was prepared from salicylic acid and 2-aminothiophenol according to the similarly reported procedure with some modifications [34]. Briefly, under N2 atmosphere, salicylic acid (5mmol) and 2-aminothiophenol (5mmol) were dissolved in polyphosphoric acid (8mL) and heated at 180°C for 5h. The mixture was cooled to room temperature and poured into 80mL ice water. The obtained solid product was further purified by column chromatography (silica gel, hexane/dichloromethane=10:1 v/v) to give 1 as white solid. Yield: 34.7%. 1H NMR (400MHz, CDCl3),δ (ppm): 12.42 (s, 1H), 8.03 (d, J=8Hz, 1H), 7.94 (d, J=8Hz, 1H), 7.74 (d, J=8Hz, 1H), 7.55 (t, J=10Hz, 1H), 7.43 (m, 2H), 7.14 (d, J=8Hz, 1H), 6.98 (t, J=8Hz, 1H); 13C NMR (100MHz, CDCl3),δ (ppm): 169.38, 157.95, 151.76, 132.79, 132.59, 128.42, 125.56, 122.16, 121.52, 119.53, 117.89, 116.77, 29.72. MALDI-TOF-MS: m/z calcd for C13H9NOS, 227.04; found, 228.09 (M+H)+.
With PPA at 140℃; for 24h;
In toluene
With polyphosphoric acid at 250℃; for 4h;
With sodium hydroxide at 250℃; for 3h; General procedure: The synthesis of 2-(2′-hydroxynaphthyl)benzothiazole (APBT), 2-(2′-hydroxyphenyl)benzothiazole (HPBT), 2-(2′-mercapto-phenyl)benzothiazole (MPBT) was carried out by condensing o-aminothiophenol (0.01 mol) with salicylic acid (0.01 mol), thiosalicylicacid (0.01 mol) and anthranilic acid (0.01) in polyphosphoric acid (PPA) (25 mL). This mixture was heated under reflux with constant stirring for 3 h at 250 °C and cooled at room temperature. The alkalinity of the resultant mixture is maintained using NaOH. The final product filtered, washed, dried and recrystallized from alcohol.
With toluene-4-sulfonic acid In ethanol for 12h; Reflux; 1.S2 The stoichiometric ratio of 2-aminobenzenethiol, salicylic acid, and p-toluenesulfonic acid were reacted in ethanol reflux for 12 hours at a stoichiometric ratio of 10:10:1. Cooled to room temperature, filtered and dried to obtain the crude product, which was purified by column chromatography (dichloromethane: petroleum ether = 1:2), the target compound 2-(2-hydroxyphenyl)benzothiazole is obtained.

Reference: [1]Wu, Yuling; Xu, Huixia; Yang, Junli; Li, Jie; Liang, Wenqing; Sun, Jing; Wang, Hua; Xu, Bingshe [New Journal of Chemistry, 2015, vol. 39, # 11, p. 8908 - 8914]
[2]Current Patent Assignee: TAIYUAN UNIVERSITY OF TECHNOLOGY - CN105085579, 2018, B Location in patent: Paragraph 0041; 0046-0049
[3]Zhou, Ji; Shi, Ruiyan; Liu, Jianxu; Wang, Rui; Xu, Yufang; Qian, Xuhong [Organic and Biomolecular Chemistry, 2015, vol. 13, # 19, p. 5344 - 5348]
[4]Meghdadi, Soraia; Amirnasr, Mehdi; Ford, Peter C. [Tetrahedron Letters, 2012, vol. 53, # 51, p. 6950 - 6953]
[5]Location in patent: experimental part Sharghi, Hashem; Asemani, Omid [Synthetic Communications, 2009, vol. 39, # 5, p. 860 - 867]
[6]Anthony, Kevin; Brown, Robert G.; Hepworth, John D.; Hodgson, Kevin W.; May, Bernadette; West, Michael A. [Journal of the Chemical Society. Perkin transactions II, 1984, p. 2111 - 2118]
[7]Santos, Fabiano S.; Ramasamy, Elamparuthi; Ramamurthy; Rodembusch, Fabiano S. [Journal of Materials Chemistry C, 2016, vol. 4, # 14, p. 2820 - 2827]
[8]Zhang, Xuan; Liu, Jing-Yun [Dyes and Pigments, 2016, vol. 125, p. 80 - 88]
[9]Billeau; Chatel; Robin; Faure; Galy [Magnetic Resonance in Chemistry, 2006, vol. 44, # 1, p. 102 - 105]
[10]Location in patent: experimental part Huixia, Xu; Bingshe, Xu; Xiaohong, Fang; Liuqing, Chen; Hua, Wang; Yuying, Hao [Journal of Photochemistry and Photobiology A: Chemistry, 2011, vol. 217, # 1, p. 108 - 116]
[11]Location in patent: experimental part Pal, Narendra; Kumar, Mahesh; Seth, Gita [E-Journal of Chemistry, 2011, vol. 8, # 3, p. 1174 - 1179]
[12]Chauhan, Manmohan Singh; Yadav, Mitlesh Kumari; Sharma, Aruna; Binani, Shradha; Lamba, Narendra Pal [Asian Journal of Chemistry, 2018, vol. 30, # 8, p. 1777 - 1780]
[13]Current Patent Assignee: HUNAN UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN111777572, 2020, A Location in patent: Paragraph 0023-0024; 0026
  • 3
  • [ 3411-95-8 ]
  • [ 557-34-6 ]
  • [ 58280-31-2 ]
YieldReaction ConditionsOperation in experiment
86% Stage #1: 2-(benzothiazol-2-yl)phenol With sodium hydroxide In methanol for 0.5h; Stage #2: zinc diacetate In methanol at 60℃; for 6h;
In not given prepared from 2-hydroxyphenyl(benzothiazole) and zinc acetate at 50°C;
  • 4
  • [ 7361-94-6 ]
  • [ 3411-95-8 ]
YieldReaction ConditionsOperation in experiment
90% With sodium hypochlorite In ethanol at 20℃; for 1h; Synthesis of SA-thiazole SA-thiazoline (2 g) and NaOCl (1 ml) were added into ethanol (20 ml). The solution was stirred at rt for 1 h and then evaporated in vacuo. The residue was dissolved in methylene dichloride (40 ml). The organic solution was washed with water (40 ml). The organic layer was dried over sodium sulfate, and then concentrated to give 1.8g product. Yield: 90%. 1H-NMR (400 MHz, DMSO-d6), δ:11.63 (s, 1H), 8.10 (m, 2H,), 7.47 (m, 4H), 7.10 (d, 1H, J = 8.08 Hz),7.01 (t, 1H, J = 7.28 Hz); 13C-NMR (100 MHz, DMSO-d6):165.83, 156.78, 151.89, 134.63, 132.93, 128.98, 126.92, 125.55, 122.56, 122.44, 120.21, 118.72, 117.44 ppm; HRMS: (C13H9NOS): calculated (MH)+: 228.0478, found 228.0478.
70% With Dowex 50W In water at 90℃; for 25h;
70% With (2,3,4,5,6-pentafluorophenyl)ammonium triflate; oxygen In water for 10h; Reflux;
810 mg With sodium cyanide In N,N-dimethyl-formamide
for 10h; UV-irradiation; 3 Synthesis of Compound IV-1: 2-(Benzo[d]thiazol-2-yl)phenol Method 1: In situ generated compound III-1 (ie, in situ-compound III-1) was subjected to photooxidation under ultraviolet light for 10 h to obtain compound IV-1 (in situ-compound IV-1).

  • 5
  • [ 1039984-47-8 ]
  • [ 3411-95-8 ]
YieldReaction ConditionsOperation in experiment
85% Stage #1: 2-hydroxy-N-(2-iodophenyl)benzamide With copper(l) iodide; sodiumsulfide nonahydrate In N,N-dimethyl-formamide at 80℃; for 12h; Stage #2: With hydrogenchloride In N,N-dimethyl-formamide at 20℃;
  • 6
  • [ 3411-95-8 ]
  • [ 13499-05-3 ]
  • [ 1210945-34-8 ]
YieldReaction ConditionsOperation in experiment
98% With piperidine In ethanol at 20℃; Inert atmosphere; Reflux; 13 To a stirred solution of hafnium chloride (2.11 g, 6.60 mmol) in ethanol (40 ml_), was added a solution of 2-(2-hydroxyphenyl)benzothiazole (6.00 g, 26.40 mmol) in ethanol (40 ml_) under nitrogen atmosphere. The pH of the reaction mixture was increased with the addition of piperidine (~15 ml_). A creamy yellow suspension was observed after a few minutes of stirring, which was refluxed for 6 hours and stirred over the weekend at room temperature. The pale yellow precipitate was filtered off, washed thoroughly with ethanol (3 x 30 ml_), dried in vacuum oven for 8 hours at 8O0C giving 6.2 g of product (98% yield). Melting point at -32O0C (broad DSC peak).
  • 7
  • scandium isopropoxide [ No CAS ]
  • [ 3411-95-8 ]
  • [ 1190879-78-7 ]
YieldReaction ConditionsOperation in experiment
100% In acetonitrile at 20℃; Inert atmosphere; Reflux; 5 To a stirred solution of scandium isopropoxide (2.00 g, 9.00 mmol) in acetonitrile (40 ml_), was added a suspension of 2-(2- hydroxyphenyl)benzothiazole (6.14 g, 27.01 mmol) in acetonitrile (40 ml_) under nitrogen atmosphere. A yellow suspension was observed after a few minutes of stirring, which was refluxed for 6 hours and stirred overnight at room temperature. The yellow solid was filtered off, washed thoroughly with acetonitrile and dried in vacuum oven at 8O0C for 8 hours giving 6.5 g of product (100% yield). Sublimation (35O0C, 10~6 Torr.) yielded an analytical sample (4.3 g from 6.3 g); melting point at 3950C (DSC peak).
  • 8
  • [ 3153-26-2 ]
  • [ 3411-95-8 ]
  • [ 11060-63-2 ]
YieldReaction ConditionsOperation in experiment
78% In tetrahydrofuran at 20℃; Inert atmosphere; Reflux; 20 To a stirred solution of vanadyl acetylacetonate (2.91 g, 10.97 mmol) in THF (30 mL), was added a suspension of 2-(2- hydroxyphenyl)benzothiazole (5.00 g, 22.00 mmol) in THF (30 mL) under nitrogen atmosphere. A brown suspension was observed after a few minutes of stirring, which was refluxed for 6 hours and stirred over the weekend at room temperature. The brown solid was filtered off, washed thoroughly with THF and dried in vacuum oven at 800C for 8 hours giving 3.1 g of product (78% yield). Sublimation (25O0C, 10~6 Torr.) yielded an analytical sample (2.6 g from 3.1 g); melting point at 4020C (DSC peak).
  • 9
  • beryllium sulfate [ No CAS ]
  • [ 3411-95-8 ]
  • [ 236753-06-3 ]
YieldReaction ConditionsOperation in experiment
100% With sodium hydroxide In methanol at 20℃; Inert atmosphere; 2 To a stirred suspension of beryllium sulfate (2.5 g, 14.11 mmol) in methanol (40 ml_), was added a solution of 2-(2- hydroxyphenyl)benzothiazole (6.42 g, 28.23 mmol) in methanol (40 ml_) at nitrogen atmosphere. The initial white suspension slowly turned to a yellowish suspension after slow addition of 1 M sodium hydroxide (50 mL), and was left vigorously stirred overnight at room temperature under nitrogen atmosphere. The yellow precipitate was filtered off, washed thoroughly with methanol (3 x 30 mL) and dried in vacuum oven for over 8 hours at 8O0C giving product 7.30 g (100% yield). It gave a blue fluorescence. Sublimation (2800C, 10"6 Torr.) yielded an analytical sample (9.3 g from 26.0 g); melting point at 33O0C (DSC peak).
  • 10
  • [ 3411-95-8 ]
  • yttrium acetylacetonate [ No CAS ]
  • [ 1210945-36-0 ]
YieldReaction ConditionsOperation in experiment
87% In acetonitrile at 20℃; Inert atmosphere; Reflux; 16 To a stirred solution of yttrium acetylacetonate (2.83 g, 7.33 mmol) in acetonitrile (30 ml_), was added a suspension of 2-(2- hydroxyphenyl)benzothiazole (5.00 g, 22.00 mmol) in acetonitrile (30 mL) under nitrogen atmosphere. A pale yellow solution was observed after a few minutes of stirring, which was refluxed for 6 hours and stirred overnight at room temperature. The pale white solid was filtered off, washed thoroughly with acetonitrile and dried in vacuum oven at 8O0C for 8 hours giving 4.9 g of product (87% yield). Sublimation (35O0C, 10~6 Torr.) yielded an analytical sample (1.4 g from 4.9 g); melting point was not observed from DSC.
  • 11
  • [ 3411-95-8 ]
  • [ 7646-85-7 ]
  • C39H24N3O3S3Zn2(1+)*Cl(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With ammonium hydroxide In ethanol; water at 20 - 60℃; 1 Preparation Example 1; Preparation of Compound (1); In ethanol (1.2 L, 0.05 M), dissolved were 2-(2-hydroxyphenyl)benzothiazole (40.0 g, 176 mmol) and ZnCl2 (16.0 g, 117.3 mmol), and the solution was stirred. To the solution, NH4OH (20 mL, 235 mmol) was added dropwise, and the resultant mixture was stirred at 60° C. under reflux for 30 minutes. After cooling the mixture to room temperature, additional NH4OH (20 mL) was added dropwise thereto, and the resultant mixture was stirred at room temperature for 12 hours. Water (400 mL) was then added, and the mixture was stirred for 6 hours, washed with water (1 L), EtOH (1.5 L) and hexane (500 mL), filtered and dried to obtain Compound (1) (35 g, 43.2 mmol, 74%).mp. >300° C.1H NMR (300 MHz, CDCl3): d=8.23-8.12 (m, 2H), 7.55 (m, 2H), 7.31 (d, J=7.7 Hz, 1H), 7.05 (t, J=7.4 Hz, 1H), 6.88 (t, J=7.7 Hz, 1H), 6.79 (d, J=7.2 Hz, 1H)MS/FAB: 805.96 (found), 809.6 (calculated)
  • 13
  • [ 3411-95-8 ]
  • [ 1656-44-6 ]
  • [ 1373156-67-2 ]
YieldReaction ConditionsOperation in experiment
80% Stage #1: 2-(benzothiazol-2-yl)phenol With triethylamine In dichloromethane at 0℃; for 0.0833333h; Stage #2: 2,4-dinitrobenzenesulfonyl chloride In dichloromethane at 0 - 20℃; for 4h; 2-(benzo[d]thiazol-2-yl)phenyl 2,4-dinitrobenzenesulfonate (1a) To a suspension of 2-(benzo[d]thiazol-2-yl)phenol (0.10 g, 0.44 mmol) in 4 mL dichloromethane, Et3N (74 μL, 0.53 mmol) was added dropwise at 0°C. The mixture was stirred for 5 min, and treated with 2,4-dinitrobenzenesulfonyl chloride (0.14 g, 0.52 mmol). The resulting mixture was stirred at room temperature for 4 h, diluted with CH2Cl2 (20 mL), washed with 1 M HCl (20 mL) and brine (20 mL), and dried over MgSO4. After solvent removal, the crude product was purified by flash chromatography (methylene chloride) on silica gel to give 0.16 g yellow product (80%). mp: 175-176 . 1H-NMR (600 MHz, DMSO): δ 7.358 (m, 1 H), 7.460 (t, J = 7.2 Hz, 2 H), 7.531 (t, J = 7.8 Hz, 1 H), 7.652 (m, 2H), 7.962 (d, J = 7.8 Hz, 1 H), 8.131 (m, 3 H), 8.607 (m, 2 H), 8.331 (dd, J1 = 2.4 Hz, J2 = 8.4 Hz, 1 H), 8.953 (d, J = 2.4 Hz, 1 H); 13C NMR (DMSO, 300 MHz): δ 161.32, 152.31, 150.75, 147.60, 145.77, 135.13, 132.94, 132.58, 131.59, 131.49, 128.99, 127.16, 126.81, 126.67, 125.91, 123.80, 123.09, 122.15, 120.66; IR (KBr, cm-1): 3110, 1607, 1600, 1541, 1388, 1344, 1191, 1093, 883, 849, 831, 779, 757, 724; HRMS m/z calcd. for C19H11N3O7S2 [(M + H)+] 458.0111; found 458.0097.
55.43% With triethylamine In dichloromethane at 20℃; 2 Example 2 Dissolve 2-(2-hydroxyphenyl)benzothiazole (0.5mmol, 0.113g) and triethylamine (1.5mmol, 0.15g) in 10mL CH2Cl2 and place them in a reaction flask.2,4-dinitrobenzenesulfonyl chloride (1mmol, 0.226g) was dissolved in 5mL CH2Cl2,At room temperature, slowly drop the acid chloride solution into the reaction flask. After the reactants are completely reacted, they are washed with 30 mL of distilled water, the organic layer is dried over anhydrous sodium sulfate, filtered, and rotary steamed to obtain a crude product. Purified by TLC (petroleum ether: ethyl acetate = 10:1), a light yellow solid is obtained, which is the target product 3-(2-benzothiazolyl)-2-phenyl-2,4-dinitrobenzenesulfonate (Compound 2), yield: 55.43%.
  • 14
  • [ 109433-86-5 ]
  • [ 2963-66-8 ]
  • [ 3411-95-8 ]
  • [ 1422198-14-8 ]
YieldReaction ConditionsOperation in experiment
83% In Dimethyl ether at 20℃; for 0.5h; 4 Synthesis of [Tb(C13H9N2O)2(C13H8NSO)]2 (19) 4.2.4 Synthesis of [Tb(C13H9N2O)2(C13H8NSO)]2 (19) A solution of Tb[N(SiMe3)2]3 (231 mg, 0.36 mmol) in DME (5 ml) was added to a solution of 2-(2-hydroxyphenyl)-1H-benzimidazole (152 mg, 0.72 mmol) and 2-(2-hydroxyphenyl)benzothiazole (82 mg, 0.36 mmol) in 10 ml DME. The reaction mixture was stirred for 30 min at room temperature, the formed precipitate was separated from the solvent by decantation, washed with cold DME and dried under vacuum to give 19 as the beige crystalline powder (241 mg, 83%). IR (ν, cm-1): 3059 (br), 1624 (w), 1603 (s), 1554 (m), 1521 (w), 1332 (m), 1318 (m), 1268 (m), 1204 (m), 1155 (w), 1133 (m), 1040 (w), 971 (w), 927 (w), 870 (m), 846 (w), 830 (w), 8026 (w), 737 (s), 6103 (w).
  • 15
  • [ 109433-86-5 ]
  • [ 3411-95-8 ]
  • [ 1422198-08-0 ]
YieldReaction ConditionsOperation in experiment
87% In Dimethyl ether at 20℃; for 0.5h; 2 Synthesis of [Сe(C13H8NSO)3]2 (2) General procedure: 4.2.2 Synthesis of [Ce(C13H8NSO)3]2 (2) A solution of Ce[N(SiMe3)2]3 (228 mg, 0.37 mmol) in DME (5 ml) was added to a solution of 2-(2-hydroxyphenyl)benzothiazole (250 mg, 1.10 mmol) in DME (10 ml). The reaction mixture was stirred for 30 min at room temperature and the solvent was separated from the precipitated solid by decantation. The precipitate was washed with cold DME and dried under vacuum to give 2 as the orange powder (249 mg, 83%). IR (ν, cm-1): 3050 (br), 1597 (s), 1554 (m), 1335 (m), 1318 (m), 1263 (w), 1216 (w), 1156 (w), 970 (w), 878 (m), 842 (m), 750 (s), 724 (s), 616 (m).
  • 16
  • tris(bis(trimethylsilyl)amido)samarium(III) [ No CAS ]
  • [ 3411-95-8 ]
  • [ 1422197-95-2 ]
YieldReaction ConditionsOperation in experiment
93% In Dimethyl ether at 20℃; for 0.5h; 2 Synthesis of [Сe(C13H8NSO)3]2 (2) General procedure: 4.2.2 Synthesis of [Ce(C13H8NSO)3]2 (2) A solution of Ce[N(SiMe3)2]3 (228 mg, 0.37 mmol) in DME (5 ml) was added to a solution of 2-(2-hydroxyphenyl)benzothiazole (250 mg, 1.10 mmol) in DME (10 ml). The reaction mixture was stirred for 30 min at room temperature and the solvent was separated from the precipitated solid by decantation. The precipitate was washed with cold DME and dried under vacuum to give 2 as the orange powder (249 mg, 83%). IR (ν, cm-1): 3050 (br), 1597 (s), 1554 (m), 1335 (m), 1318 (m), 1263 (w), 1216 (w), 1156 (w), 970 (w), 878 (m), 842 (m), 750 (s), 724 (s), 616 (m).
  • 17
  • [ 3411-95-8 ]
  • tris(bis(trimethylsilyl)amido)europium(III) [ No CAS ]
  • [ 1422198-01-3 ]
YieldReaction ConditionsOperation in experiment
86% In Dimethyl ether at 20℃; for 0.5h; 2 Synthesis of [Сe(C13H8NSO)3]2 (2) General procedure: 4.2.2 Synthesis of [Ce(C13H8NSO)3]2 (2) A solution of Ce[N(SiMe3)2]3 (228 mg, 0.37 mmol) in DME (5 ml) was added to a solution of 2-(2-hydroxyphenyl)benzothiazole (250 mg, 1.10 mmol) in DME (10 ml). The reaction mixture was stirred for 30 min at room temperature and the solvent was separated from the precipitated solid by decantation. The precipitate was washed with cold DME and dried under vacuum to give 2 as the orange powder (249 mg, 83%). IR (ν, cm-1): 3050 (br), 1597 (s), 1554 (m), 1335 (m), 1318 (m), 1263 (w), 1216 (w), 1156 (w), 970 (w), 878 (m), 842 (m), 750 (s), 724 (s), 616 (m).
  • 18
  • tris[N,N-bis(trimethylsilyl)amide]gadolinium(III) [ No CAS ]
  • [ 3411-95-8 ]
  • [ 1422198-04-6 ]
YieldReaction ConditionsOperation in experiment
91% In Dimethyl ether at 20℃; for 0.5h; 2 Synthesis of [Сe(C13H8NSO)3]2 (2) General procedure: 4.2.2 Synthesis of [Ce(C13H8NSO)3]2 (2) A solution of Ce[N(SiMe3)2]3 (228 mg, 0.37 mmol) in DME (5 ml) was added to a solution of 2-(2-hydroxyphenyl)benzothiazole (250 mg, 1.10 mmol) in DME (10 ml). The reaction mixture was stirred for 30 min at room temperature and the solvent was separated from the precipitated solid by decantation. The precipitate was washed with cold DME and dried under vacuum to give 2 as the orange powder (249 mg, 83%). IR (ν, cm-1): 3050 (br), 1597 (s), 1554 (m), 1335 (m), 1318 (m), 1263 (w), 1216 (w), 1156 (w), 970 (w), 878 (m), 842 (m), 750 (s), 724 (s), 616 (m).
  • 19
  • [ 132656-41-8 ]
  • [ 3411-95-8 ]
  • [ 1422198-11-5 ]
YieldReaction ConditionsOperation in experiment
86% In Dimethyl ether at 20℃; for 0.5h; 2 Synthesis of [Сe(C13H8NSO)3]2 (2) General procedure: 4.2.2 Synthesis of [Ce(C13H8NSO)3]2 (2) A solution of Ce[N(SiMe3)2]3 (228 mg, 0.37 mmol) in DME (5 ml) was added to a solution of 2-(2-hydroxyphenyl)benzothiazole (250 mg, 1.10 mmol) in DME (10 ml). The reaction mixture was stirred for 30 min at room temperature and the solvent was separated from the precipitated solid by decantation. The precipitate was washed with cold DME and dried under vacuum to give 2 as the orange powder (249 mg, 83%). IR (ν, cm-1): 3050 (br), 1597 (s), 1554 (m), 1335 (m), 1318 (m), 1263 (w), 1216 (w), 1156 (w), 970 (w), 878 (m), 842 (m), 750 (s), 724 (s), 616 (m).
  • 20
  • [ 41836-21-9 ]
  • [ 3411-95-8 ]
  • [ 1422197-90-7 ]
YieldReaction ConditionsOperation in experiment
83% In Dimethyl ether at 20℃; for 0.5h; 2 Synthesis of [Сe(C13H8NSO)3]2 (2) General procedure: 4.2.2 Synthesis of [Ce(C13H8NSO)3]2 (2) A solution of Ce[N(SiMe3)2]3 (228 mg, 0.37 mmol) in DME (5 ml) was added to a solution of 2-(2-hydroxyphenyl)benzothiazole (250 mg, 1.10 mmol) in DME (10 ml). The reaction mixture was stirred for 30 min at room temperature and the solvent was separated from the precipitated solid by decantation. The precipitate was washed with cold DME and dried under vacuum to give 2 as the orange powder (249 mg, 83%). IR (ν, cm-1): 3050 (br), 1597 (s), 1554 (m), 1335 (m), 1318 (m), 1263 (w), 1216 (w), 1156 (w), 970 (w), 878 (m), 842 (m), 750 (s), 724 (s), 616 (m).
  • 21
  • [ 3411-95-8 ]
  • [ 100-97-0 ]
  • [ 1428114-89-9 ]
YieldReaction ConditionsOperation in experiment
72% With trifluoroacetic acid for 8h; Reflux; 5-(Benzo[d]thiazol-2-yl)-4-hydroxyisophthalaldehyde (3). A mixture of benzo[d]thiazolylphenol 4 (2.28 g, 10 mmol), hexamethylenetetramine (8.40 g, 60 mmol) and trifluoroacetic acid (30 mL) was refluxed for 8 h, cooled, and a mixture of conc. HCl (14 mL) and H2O (28mL) was added. The reaction mixture was poured into H2O (130 mL),the solid was filtered off, washed with water, dried and recrystalized from chlorobenzene. Yield 72%, m.p. 196-197 oC. 1H NMR (300 MHz,CDCl3, δ ): 7.50 (1, dt, J 7.7 Hz, J 1.2 Hz, H-5' ); 7.58 (1, dt, J 7.8 Hz, J 1.2 Hz, H-6' ); 7.98 (1, dd, J 7.9 Hz, J 0.6 Hz, H-4' ); 8.05(1, dd, J 7.8 Hz, J 0.9 Hz, H-7' ); 8.41 (1, d, J 1.9 Hz, H-6); 8.55(1, d, J 2.1 Hz, H-4); 9.99 (1, s, 3-CO); 10.60 (1, s, 1-CO);14.21 (1, s, 4-). Elemental analyses: Found: C, 63.66; H, 3.11; N,4.81%; C15H9NO3S; requires: C, 63.59; H, 3.20; N, 4.94%.
24% With trifluoroacetic acid at 0 - 145℃; for 36.5h; Inert atmosphere;
With acetic acid In toluene Reflux;
With trifluoroacetic acid for 36h; Inert atmosphere; Reflux;

  • 22
  • [ 90-02-8 ]
  • [ 105-56-6 ]
  • [ 137-07-5 ]
  • [ 3411-95-8 ]
YieldReaction ConditionsOperation in experiment
65% In butan-1-ol for 7h; Reflux; 2-Benzothiazolyl phenol General procedure: Salicylaldehyde (2 mmol), ethyl cyanoacetate (2 mmol), and o-aminophenol(2 mmol) were mixed in n-BuOH (20 mL), and the solution was refluxed for 7 h.The solvent was removed, and the residue was suspended in EtOH (10 mL) and stirred with 1 % NaOH (10 mL) for 30 min. After filtration and washing with water,the product was obtained as yellow solid.
62% With benzoic acid In butan-1-ol at 110℃; for 8h; Synthesis of compounds BTP and BTN General procedure: A mixture of appropriate aromatic aldehyde (24 mmol), ethyl cyanoacetate (24 mmol), o-aminothiophenol (24 mmol) and benzoic acid (12 mmol) in n-butanol (50 mL) was dissolved in 1-butanol (50 mL). The mixture solution was refluxed for 8 h. After the solvent was partly evaporated under reduced pressure, the reaction mixture was cooled to room temperature. 100 mL NaOH (2%) was added into the mixture and stirring about 0.5 h. The yellow solid powder was obtained by filtering. There are two products in the solid, one is a large amount of green fluorescent product, and the other is a less amount of blue fluorescent product. The crude was purified by chromatography on silica gel using ethyl acetate/petroleum ether (1:8, v/v) as the eluent to obtain the green fluorescent product.
  • 23
  • [ 3411-95-8 ]
  • [ 100-51-6 ]
  • [ 1002026-30-3 ]
YieldReaction ConditionsOperation in experiment
60% With tert.-butylhydroperoxide; copper(II) ferrite In para-xylene; water at 100℃; for 24h;
57% With tert.-butylhydroperoxide; copper diacetate In water; dimethyl sulfoxide at 80℃; for 20h; Sealed tube; 15 Typical procedure for the esterification of 2-carbonyl substituted phenols General procedure: To an oven-dried sealed tube charged with 2-hydroxyacetophenone (1a) (40.8mg, 0.3mmol, 1.0equiv), Cu(OAc)2 (2.7mg, 0.015mmol, 5mol%), and TBHP (70% in water) (0.16mL, 1.2mmol, 4.0equiv) in DMSO (1mL, 0.3M) was added benzyl alcohol (2a) (65.4mg, 0.6mmol, 2equiv). The reaction mixture was allowed to stir at 80°C for 20h. After cooling at room temperature, the reaction mixture was evaporated onto silica gel. Purification of the product by column chromatography (SiO2: n-hexanes/EtOAc=40:1) provided 3a (50.5mg) in 70% yield 4.2.15 2-(Benzo[d]thiazol-2-yl)phenyl benzoate (3o) Light yellow solid; mp 144-147 °C; Rf=0.40 (n-hexanes/EtOAc=5:1); 1H NMR (700 MHz, CDCl3) δ 8.40 (d, J=7.8 Hz, 1H), 8.31 (d, J=8.2 Hz, 2H), 7.91 (d, J=8.0 Hz, 1H), 7.78 (d, J=8.0 Hz, 1H), 7.68 (t, J=7.5 Hz, 1H), 7.56-7.53 (m, 3H), 7.44-7.40 (m, 2H), 7.33-7.31 (m, 2H); 13C NMR (175 MHz, CDCl3) δ 165.0, 162.2, 152.8, 148.5, 135.3, 133.7, 131.4, 130.6, 130.2, 129.4, 128.6, 126.4, 126.3, 126.1, 125.1, 123.8, 123.2, 121.3; IR (KBr) ν 2917, 1742, 1601, 1482, 1449, 1314, 1259, 1191, 1176, 1104, 1054, 1022, 966 cm-1; HRMS (EI) calcd for C20H13NO2S [M]+ 331.0667, found 331.0659.
  • 24
  • [ 3411-95-8 ]
  • [bis(2,4,4,9-tetramethyl-1,5,9-triazacyclododec-1-ene)bis(μ-hydroxo)dinickel(II)] hexafluorophosphate [ No CAS ]
  • [Ni(Me4-mcN3)(hpbt)](PF6) [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% In acetone at 20℃; for 2h; 2.3 Syntheses General procedure: In separate experiments, the corresponding benzazole (0.232 mmol) was added to a solution of [Ni(Me3-mcN3)(μ-OH)]2(PF6)2 (100 mg, 0.116 mmol) in acetone (20 mL). The reaction mixture was stirred at room temperature for 2 h. The solution was concentrated to approximately 5 mL and Et2O (25 mL) was added. The resulting precipitate was filtered and the green solid was washed with several aliquots of diethyl ether and vacuum-dried to give the expected complexes 1a-3a. The powder isolated in each case was air stable
  • 25
  • [ 3411-95-8 ]
  • [bis(2,4,4-trimethyl-1,5,9-triazacyclododec-1-ene)bis(μ-hydroxo)dinickel(II)] hexafluorophosphate [ No CAS ]
  • [Ni(2,4,4-trimethyl-1,5,9-triazacyclododec-1-ene)(2-(2'-hydroxy phenyl)benzothiazolate)](PF6) [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% In acetone at 20℃; for 2h; 2.3 Syntheses In separate experiments, the corresponding benzazole (0.232 mmol) was added to a solution of [Ni(Me3-mcN3)(μ-OH)]2(PF6)2 (100 mg, 0.116 mmol) in acetone (20 mL). The reaction mixture was stirred at room temperature for 2 h. The solution was concentrated to approximately 5 mL and Et2O (25 mL) was added. The resulting precipitate was filtered and the green solid was washed with several aliquots of diethyl ether and vacuum-dried to give the expected complexes 1a-3a. The powder isolated in each case was air stable
  • 26
  • [ 3411-95-8 ]
  • [ 31643-49-9 ]
  • [ 1578263-21-4 ]
YieldReaction ConditionsOperation in experiment
97% Stage #1: 2-(benzothiazol-2-yl)phenol; 4-Nitrophthalonitrile In N,N-dimethyl-formamide at 50℃; for 0.166667h; Inert atmosphere; Stage #2: With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 122h; Inert atmosphere; 2.3.1 Preparation of 4-(2-(benzo[d]thiazol-2-yl)phenoxy)phthalonitrile (3) A solution of 2-(benzo[d]thiazol-2-yl)phenol (1) (1g, 4.4mmol) and 4-nitro phthalonitrile (0.76g, 4.4mmol) (2) in dry DMF (15mL) was stirred at 50°C for 10min under a nitrogen atmosphere. And then, finely ground anhydrous K2CO3 (2.43g, 17.6mmol) was added portionwise over a period of 2h with stirring at this temperature. After stirring for 120h at 50°C, the reaction mixture was poured over crushed ice and the resulting white precipitate was filtered off, washed with distilled water, and then dried in vacuo. Yield: 1.5g (97%), m.p.: 177-179°C. Calc. for C21H11N3OS: % C 71.37, % H 3.14, % N 11.89. Found: % C 71.39, % H 3.19, % N 11.85. FT-IR νmax/cm-1 : 3070 (Ar-H), 2234 (C≡N), 1601, 1561 (C=N), 1485, 1251 (Ar-O-C), 1105, 955, 837, 759, 694 (C-S). 1H NMR (CDCl3) (δ: ppm): 8.60 (ArH, 1H, d), 8.11 (Ar-H, 1H, d), 7.91 (ArH, 1H, d), 7.75 (ArH, 1H, d), 7.53-7.22 (ArH, 7H, m). 13C NMR (CDCl3) (δ: ppm): 161.01, 152.68, 151.14, 135.79, 132.70, 131.30, 127.33, 126.79, 125.91, 123.65, 122.06, 121.87, 121.68, 121.43, 118.12, 115.44, 115.06, 109.92. MALDI-TOF, m/z: Calc.: 353.40; Found: 353.12 [M]+.
  • 27
  • [ 3411-95-8 ]
  • [ 109-63-7 ]
  • 2-(2-difluoroboranyloxy-phenyl)-benzothiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; 2.5 General procedure for the preparation and characterization of F-B complexes General procedure: The synthetic routes for these F-B complexes are depicted in Scheme 1. The corresponding 2-hydroxybenzothiazole and 2-hydroxybenzoxazole were synthesized following the literature methods [26,27]. R1-R3 have been previously reported, and here they were synthesized as reference complexes for comparison with the optical properties of the structurally related F-B complexes [23,25,28]. Portions of 2-hydroxybenzothiazole or 2-hydroxybenzoxazole (2.0mmol) and N,N’-diisopropylethylamine (DIEA) (0.5mL) were dissolved in 20mL of dichloromethane. BF3·Et2O (2.0mL) was added dropwise at room temperature. A yellowish precipitate formed immediately. After the disappearance of the 2-hydroxybenzothiazole or 2-hydroxybenzoxazole, as monitored by TLC, the yellowish solid was filtered and washed thoroughly with dichloromethane. The crude product was purified by silica gel (200-300 mesh) column chromatography (eluent: CH2Cl2 and hexane).
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h; Inert atmosphere;
  • 28
  • [ 617-84-5 ]
  • [ 3411-95-8 ]
  • 2-(benzo[d]thiazol-2-yl)phenyl diethylcarbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With tert.-butylhydroperoxide; copper ferrite In water at 100℃; for 2h;
75% With tert.-butylhydroperoxide; copper(II) ferrite In water for 2h; Heating; Catalytic studies The CuFe2O4 superparamagnetic nanoparticles were supplied by Sigma-Aldrich. The catalyst was subsequently characterized by various analytical protocols. In an representative experiment, 2-(2-hydroxyphenyl)benzothiazole (0.1136 g, 0.5 mmol) was dissolved in N,N’-dimethylformamide (DMF, 1.5 mL, 19 mmol), and the solution added into a 8 mL vial consisting of the pre-calculated quantity of catalyst. The catalyst amount was determined with respect to the copper/2-(benzo[d]thiazol-2-yl)phenol mole ratio. Subsequently, tert-butyl hydroperoxide (tBuOOH, 70% wt. in water; 0.0727 mL, 0.5 mmol) was added to the vial, and the resulting mixture magnetically stirred at 100 oC for 60 min under air. Next, the reactor was cooled to room temperature, and diphenyl ether (0.0851 g, 0.5 mmol) as an internal standard was added to the reaction mixture. Samples were taken, diluted with ethyl acetate (3 mL), stirred carefully with anhydrous Na2SO4 to remove water residue, and analyzed by GC regarding diphenyl ether internal standard. The o-(2-benzothiazolyl)phenyl dimethylcarbamate was purified using column chromatography and the product identity confirmed by GC-MS, 1H NMR and 13C NMR.
71% With tert.-butylhydroperoxide; copper diacetate In water at 80℃; Green chemistry;
  • 29
  • [ 3411-95-8 ]
  • [ 2700-30-3 ]
  • 2-(benzo[d]thiazol-2-yl)phenyl diisopropylcarbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With tert.-butylhydroperoxide; copper(II) ferrite; In water; for 2h;Heating; The CuFe2O4 superparamagnetic nanoparticles were supplied by Sigma-Aldrich. The catalyst was subsequently characterized by various analytical protocols. In an representative experiment, 2-(2-hydroxyphenyl)benzothiazole (0.1136 g, 0.5 mmol) was dissolved in N,N?-dimethylformamide (DMF, 1.5 mL, 19 mmol), and the solution added into a 8 mL vial consisting of the pre-calculated quantity of catalyst. The catalyst amount was determined with respect to the copper/2-(benzo[d]thiazol-2-yl)phenol mole ratio. Subsequently, tert-butyl hydroperoxide (tBuOOH, 70% wt. in water; 0.0727 mL, 0.5 mmol) was added to the vial, and the resulting mixture magnetically stirred at 100 oC for 60 min under air. Next, the reactor was cooled to room temperature, and diphenyl ether (0.0851 g, 0.5 mmol) as an internal standard was added to the reaction mixture. Samples were taken, diluted with ethyl acetate (3 mL), stirred carefully with anhydrous Na2SO4 to remove water residue, and analyzed by GC regarding diphenyl ether internal standard. The o-(2-benzothiazolyl)phenyl dimethylcarbamate was purified using column chromatography and the product identity confirmed by GC-MS, 1H NMR and 13C NMR.
  • 30
  • [ 2591-86-8 ]
  • [ 3411-95-8 ]
  • 2-(benzo[d]thiazol-2-yl)phenyl piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With tert.-butylhydroperoxide; copper(II) ferrite In water for 2h; Heating; Catalytic studies The CuFe2O4 superparamagnetic nanoparticles were supplied by Sigma-Aldrich. The catalyst was subsequently characterized by various analytical protocols. In an representative experiment, 2-(2-hydroxyphenyl)benzothiazole (0.1136 g, 0.5 mmol) was dissolved in N,N’-dimethylformamide (DMF, 1.5 mL, 19 mmol), and the solution added into a 8 mL vial consisting of the pre-calculated quantity of catalyst. The catalyst amount was determined with respect to the copper/2-(benzo[d]thiazol-2-yl)phenol mole ratio. Subsequently, tert-butyl hydroperoxide (tBuOOH, 70% wt. in water; 0.0727 mL, 0.5 mmol) was added to the vial, and the resulting mixture magnetically stirred at 100 oC for 60 min under air. Next, the reactor was cooled to room temperature, and diphenyl ether (0.0851 g, 0.5 mmol) as an internal standard was added to the reaction mixture. Samples were taken, diluted with ethyl acetate (3 mL), stirred carefully with anhydrous Na2SO4 to remove water residue, and analyzed by GC regarding diphenyl ether internal standard. The o-(2-benzothiazolyl)phenyl dimethylcarbamate was purified using column chromatography and the product identity confirmed by GC-MS, 1H NMR and 13C NMR.
62% With tert.-butylhydroperoxide; copper diacetate In water at 80℃; Green chemistry;
61% With tert.-butylhydroperoxide; copper ferrite In water at 100℃; for 2h;
  • 31
  • [ 4394-85-8 ]
  • [ 3411-95-8 ]
  • 2-(benzo[d]thiazol-2-yl)phenyl morpholine-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With tert.-butylhydroperoxide; copper(II) ferrite In water for 2h; Heating; Catalytic studies The CuFe2O4 superparamagnetic nanoparticles were supplied by Sigma-Aldrich. The catalyst was subsequently characterized by various analytical protocols. In an representative experiment, 2-(2-hydroxyphenyl)benzothiazole (0.1136 g, 0.5 mmol) was dissolved in N,N’-dimethylformamide (DMF, 1.5 mL, 19 mmol), and the solution added into a 8 mL vial consisting of the pre-calculated quantity of catalyst. The catalyst amount was determined with respect to the copper/2-(benzo[d]thiazol-2-yl)phenol mole ratio. Subsequently, tert-butyl hydroperoxide (tBuOOH, 70% wt. in water; 0.0727 mL, 0.5 mmol) was added to the vial, and the resulting mixture magnetically stirred at 100 oC for 60 min under air. Next, the reactor was cooled to room temperature, and diphenyl ether (0.0851 g, 0.5 mmol) as an internal standard was added to the reaction mixture. Samples were taken, diluted with ethyl acetate (3 mL), stirred carefully with anhydrous Na2SO4 to remove water residue, and analyzed by GC regarding diphenyl ether internal standard. The o-(2-benzothiazolyl)phenyl dimethylcarbamate was purified using column chromatography and the product identity confirmed by GC-MS, 1H NMR and 13C NMR.
59% With tert.-butylhydroperoxide; copper diacetate In water at 80℃; Green chemistry;
50% With tert.-butylhydroperoxide; copper ferrite In water at 100℃; for 2h;
  • 32
  • [ 3411-95-8 ]
  • [ 76-05-1 ]
  • 3-(benzo[d]thiazol-2-yl)-2-hydroxybenzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With hexamethylenetetramine; silica gel for 3h; Milling; Sealed tube; a) Synthesis of 3-(benzothiazol-2-yl)hydroxybenzaldehyde (2). First, the commercially available 2-(2-hydroxyphenyl)benzothiazole (1)was synthesized in the laboratory using our previously reported mechanochemicalmethod [61]. Next, a mixture of benzothiazole 1 (454 mg,2.0 mmol), hexamethylenetetramine (420 mg, 3.0 mmol), trifluoroaceticacid (0.76 mL, 10 mmol) and silica gel (60-120 mesh) (1.3 g, 3times of the weight of 1) were taken in a 5 mL stainless steel (SS) millingjar containing an SS ball (10 mm). The jar was capped properly and thereaction mixture was subjected to milling in MM400 at 30 Hz for 3 h.After completion of the reaction, as revealed by TLC, the finelypowdered reaction mixture in silica matrix was purified by flash chromatographyeluting with EtOAc-petroleum ether (1:20) to afford thepure product (2) [62] as yellow crystalline solid (401 mg, yield: 78 %),mp. 135 137 C; 1H NMR (400 MHz, DMSO-d6): (ppm) 12.94 (s, 1H,exchangeable), 10.35 (s, 1 H), 8.34 (d, 1H, J = 7.2 Hz), 8.17 (t, 1H,J = 8 Hz), 8.10 (d, 1H, J = 8 Hz), 7.90 (d, 1H, J = 8 Hz), 7.60 7.45 (m,2 H), 7.23 (td, 1H, J1 = 1.6 Hz, J2 = 7.6 Hz); 13C NMR (100 MHz,DMSO-d6): (ppm) 192.2, 165.8, 161.4, 151.4, 135.5, 133.4, 132.1,127.4, 126.4, 123.9, 122.8, 120.7, 119.6, 118.0; HRMS (ESI-TOF): m/zcalcd for C14H9NO2S [M+H]+ 256.0427, found 256.0381
56% With hexamethylenetetramine for 8h; Reflux; 2.2 Preparation of aldehyde derivative 2 Aldehyde derivative 2 was prepared by the reaction of commercial ESIPT dye 1 with hexamethylenetetramine (HMTA) and trifluoroacetic acid (TFA) following a previously reported method [37]. 2-(2-Hydroxyphenyl)benzothiazole 1 (454 mg, 2.0 mmol) and HMTA (280 mg, 2.0 mmol) were dissolved in TFA (10 mL), and the reaction mixture was stirred under reflux for 8 h. After cooling, the mixture was neutralized using 1.0 N NaOH solution. The resulting precipitate was filtered, washed with distilled water several times, and dried. Purification of the dried precipitate was carried out by column chromatography (silica gel, hexane:ethyl acetate = 3:1, v/v) to obtain aldehyde derivative 2 as a light yellow powder (280 mg, yield: 56%). 1H NMR (300 MHz, DMSO-d6) δ 12.98 (s, 1H), 10.35 (s, 1H), 8.38 (d, J = 8.0 Hz, 1H), 8.19 (d, J = 8.1 Hz, 1H), 8.11 (d, J = 8.2 Hz, 1H), 7.90 (d, J = 7.9 Hz, 1H), 7.53 (dt, J = 25.7, 7.7 Hz, 2H), 7.21 (t, J = 7.9 Hz, 1H). LRMS: (DIP+); m/z calcd for C14H9NO2S+ [M]+: 255.0, found 255.0.
With hexamethylenetetramine
With hexamethylenetetramine
With hexamethylenetetramine Reflux;

  • 33
  • [ 462-08-8 ]
  • [ 3411-95-8 ]
  • C18H12N4OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% Stage #1: pyridin-3-ylamine With hydrogenchloride In water at 0 - 5℃; for 0.25h; Stage #2: 2-(benzothiazol-2-yl)phenol With sodium hydroxide; sodium nitrite In tetrahydrofuran; water for 4h; 2.1 Synthesis of chemosensor 1 The synthesis of chemosensor 1 is depicted in Scheme 1.The diazo-coupling reaction of benzimidazole derivativeresults in formation of chemosensor 1. 3-Aminopyridine (0.094 g, 1 mmol) was suspended in30.0mL of distilled water at the temperature of 0-5°C.Then 1.0mL of HCl solution was added to the mixture.After 15 min, aqueous solution of sodium nitrite (0.076 g,1.1mmol) was added, followed by addition of THFsolution of 2-(2-hydroxyphenyl)benzothiazole (0.227 g,1mmol) and then pH was adjusted to 8-9 with NaOHsolution (16). After stirring for 4 h, the solution wasneutralised with HCl solution. The produced precipitatewas filtered and washed several times with water and driedat vacuum. Column chromatography was performed toobtain pure azo compound (1) in a yield of 60%. Off-whitesolid; m.p. 182°C; IR (cm21) 3089 (nCZHstr.aromatic), 1626(νCvNstr.); 1H NMR (DMSO, 400 MHz) δ (ppm): 12.4(brs, 1H, phenolic ZOH, exchanges with D2O), 9.1 (s, 1H,ArH), 8.90 (s,1H, ArH), 8.70 (d, 1H, J 6.0 Hz, ArH),8.21 (d, 2H, J 6.0 Hz, ArH), 8.17 (t, 3H, J1, J2 6.0 Hz, ArH), 8.11 (d, 1H, J 6.0 Hz, ArH), 8.03 (d,1H, J 6.0 Hz, ArH), 7.62 (d, 1H, J 6.0 Hz, ArH);13CNMR (CDCl3, 100 MHz) δ (ppm): 168.70, 161.15, 151.54,151.37, 147.84, 147.17, 145.66, 132.68, 126.99, 126.83,126.50, 126.01, 125.13, 124.03, 122.33, 121.71, 118.84,116.87; MS: m/z (relative abundance (%), assignment) 333 [100, (M 1)]; HR-MS: 333 [(M 1)]Elemental analysis calcd for C18H12N4OS: C, 65.04; H,3.64; N, 16.86. Found: C, 65.12; H, 3.70; N, 16.79.
  • 34
  • [ 3411-95-8 ]
  • [ 94847-10-6 ]
  • 2-[2-(6-(9-carbazolyl)hexyl)phenyl]benzothiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% Stage #1: 2-(benzothiazol-2-yl)phenol; N-(6-bromohexyl)carbazole With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; Stage #2: In water; N,N-dimethyl-formamide for 24h; Reflux; Inert atmosphere;
  • 35
  • [ 69-72-7 ]
  • [ 1141-88-4 ]
  • [ 3411-95-8 ]
  • C20H15NO4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% Stage #1: salicylic acid; 2-Aminophenyl disulfide In toluene at 70℃; for 2.5h; Inert atmosphere; Stage #2: With phosphorus trichloride In toluene at 30 - 100℃; Inert atmosphere; General procedure for the synthesis of benzothiazole derivatives 3a-3p, D. General procedure: 2,2'-Disulfanediyldianiline 1a or 6,6'-disulfanediylbis(3-chloroaniline) 1b (0.5 mmol) and carboxylic acid (1.0 mmol, except 0.5mmol for 2k) were added to a three-neck flask under an atmosphere of Ar, and 5 mL dry toluene was added, then the mixture was stirred for 2.5 h at 70 °C to allow the solid to dissolve in toluene solvent completely. After the reaction solution was cooled down to 30 °C, PCl3 (1.2 mmol, 0.165 g) was added dropwise. When the PCl3 was added completely, the reaction mixture was further stirred for 4 - 6 h at 100°C until no 2,2'-disulfanediyldianiline or 6,6'-disulfanediylbis(3-chloroaniline) was detected by TLC analysis. The reaction solution was washed with saturated aqueous sodium bicarbonate solution and extracted with CH2Cl2. The collected organic layers were dried over anhydrous MgSO4. After filtered toremove the MgSO4 and the solvent was removed under reduced pressure. The crude product was purifiedby flash chromatography on silica gel using PE / EtOAc.
  • 36
  • [ 3411-95-8 ]
  • [ 993-12-4 ]
  • C15H14NOPS2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With triethylamine In dichloromethane at 25℃; for 12h;
65% With triethylamine In dichloromethane at 20℃; for 4h; Synthesis of Probe BTP The synthetic routine of probe BTP is outlined in Scheme 1.HBTwas synthesized by a similar way described in a reportedmethod [26]. Dimethylthiophosphinoyl chloride (105 μL,1 mmol) in 20 mL dichloromethane was added to a mixtureof HBT (136 mg, 0.60 mmol) and triethylamine (138 μL,1 mmol) in 20 mL dichloromethane. The reaction mixturewas stirred at room temperature for 4 h, and concentratedunder reduced pressure. The crude product was purified bycolumn chromatography (silica gel, hexane/ethyl acetate =2/1) to afford BTP (124 mg, 65 %) as a white powder. 31PNMR(162 MHz, CDCl3): δ = 96.16 ppm. 1H NMR (400 MHz,CDCl3, ppm) δ: 2.11 (d, 3 H, J = 4 Hz), 2.13 (d, 3 H,J = 4 Hz),7.35 (t, 1 H, J = 8 Hz), 7.50 (m, 3 H), 7.88 (d, 1H, J = 8 Hz), 7.96 (d, 1 H, J = 8 Hz), 8.13 (d, 1 H, J = 8 Hz),8.33 (d, 1 H, J = 4 Hz); 13C NMR (100 MHz, CDCl3, ppm) δ:23.88, 24.61, 121.40, 121.69, 121.74, 123.31, 125.21, 125.38,125.84, 125.89, 126.41, 130.81, 131.47, 135.54, 148.80,148.89, 152.63, 162.45; HR-MS m/ z : Calcd forC15H15NOPS2+ ([M + H+]+) 320.0333, found 320.0315[M + H+]+, 342.0129 [M+ Na+]+.
  • 37
  • [ 3411-95-8 ]
  • [ 289712-57-8 ]
  • C21H14N4O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 8h; Inert atmosphere; 1.6 (6) Synthesis of compound FN3-H2S A solution of compound 1-4 (9.1 mg, 0.528 mmol, 1 eq), compound 2-1 (100 mg, 0.528 mmol, 1 eq), DMAP (201 mg, 0.528 mmol, 1 eq, DCC (136 mg, 0.528 mmol, Methylene chloride, protected by nitrogen and reacted at room temperature for 8 hours at room temperature. The reaction was carried out using TCL plate. After completion of the reaction, the crude product was distilled off under reduced pressure and the residue was separated on a silica gel column with a silica particle size of 200-300 mesh. 1H-NMR (400 MHz, DMSO-d6) (see Fig. 1)? 8.40 (d, J = 7.4 Hz, 1H). The yield of the probe was 81%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;
  • 38
  • [ 3411-95-8 ]
  • tert-butyl {(2S)-1-[4-(chloromethyl)anilino]-1-oxopropan-2-yl}carbamate [ No CAS ]
  • tert-butyl N-[(1S)-1-({4-[2-(1,3-benzothiazol-2-yl)phenoxymethyl]phenyl}carbamoyl)ethyl]carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With caesium carbonate In N,N-dimethyl-formamide at 90℃; for 6h; 9 5.10. tert-butyl N-[(1S)-1-({4-[2-(1,3-benzothiazol-2-yl)phenoxymethyl]phenyl}carbamoyl)ethyl]carbamate A mixture of 2-(2-hydroxyphenyl)benzothiazole 16d (0.33 g,1.47 mmol), compound 15 (0.46 g, 1.47 mmol) and Cs2CO3(0.48 g, 1.47 mmol) was stirred (6 h) in dry DMF (20 mL) at 90 °C.The mixture was allowed to cool to room temperature and the solventwas evaporated. EtOAc (30 mL) was added to the residue and the resulting mixture was washed successively with 10% aq NaHCO3 solution (40 mL) and water (40 mL). The organic fraction was dried (MgSO4) and evaporated. The residue was purified by column chromatography (SiO2, CH2Cl2 changing to CH2Cl2-MeOH(98:2)) giving compound 17d as a white powder (0.27 g, 84%),mp 102 °C; 1H NMR (400 MHz, d6-DMSO) d 10.04 (1H, s, NH),8.46 (1H, dd, J = 7.8 and 1.8 Hz, Ar-H), 8.12-8.03 (2H, m, Ar-H),7.67 (2H, d, J = 8.7 Hz, Ar-H), 7.57-7.50 (4H, m, Ar-H), 7.44-7.38(2H, m, Ar-H), 7.17 (1H, t, J = 7.1 Hz, Ar-H), 7.12 (1H, J = 7.3 Hz,NH), 5.39 (2H, s, CH2), 4.13 (1H, dt, J = 7.1 Hz, CH), 1.39 (9H, s,3 CH3), 1.27 (3H, d, J = 6.9 Hz, CH3);13C NMR (101 MHz, d6-DMSO) d 172.5 (CO), 162.7 (CO), 156.4 (Ar-C), 155.7 (Ar-C),152.0 (Ar-C), 139.6 (Ar-C), 136.0 (Ar-C), 132.8 (Ar-C), 131.2 (Ar-C), 129.5 (2 Ar-C), 129.4 (Ar-C), 126.8 (Ar-C), 125.4 (Ar-C),122.9 (Ar-C), 122.4 (Ar-C), 122.0 (Ar-C), 121.7 (Ar-C), 119.6(2 Ar-C), 114.4 (Ar-C), 78.6 (C(CH3)3), 70.7 (CH2O), 51.0 (CHCH3),28.7 (C(CH3)3), 18.5 (CH3); IR mmax 3360-3250 (br, NH), 2982, 1669(CO), 1601 (CO), 1510, 1499, 1244, 1161, 754 cm1; LRMS calcdfor C28H29N3O4SNa [M+Na]+ 526.60; found 526.13.
  • 39
  • [ 3411-95-8 ]
  • [ 572-09-8 ]
  • [2-(benzothiazol-2'-yl)-phenolyl] 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% Stage #1: 2-(benzothiazol-2-yl)phenol With potassium phosphate; tetrabutylammomium bromide In dichloromethane; water at 25 - 28℃; for 0.166667h; Inert atmosphere; Stage #2: 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide In dichloromethane; water for 7h; Inert atmosphere; Reflux;
74% Stage #1: 2-(benzothiazol-2-yl)phenol With potassium phosphate; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane; water at 20℃; for 0.166667h; Inert atmosphere; Stage #2: 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide In dichloromethane; water for 7h; Reflux; 4.1 (1) glycosylation reaction To a solution of 2- (benzothiazol-2-yl) phenol (1135 mg, 5.00 mmol), TBAHS (400 mg, 1.00 mmol) and K3PO4 (5307 mg, 25.00 mmol) was added H20 [265 μL, 5% (w / w)] followed by CH2Cl2 (50 mL) and stirred at room temperature for about 10 min under argon protection. 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (5140 mg, 12.50 mmol) was then added in one portion and the reaction was stirred for 7 h under reflux with heating. The liquid was separated and the resulting organic phase was dried over anhydrous sodium sulfate, concentrated and separated on a silica gel column. The residue was recrystallized from ethanol and dried in vacuo to give the title compound (2064 mg, 74% yield) as a white powder. The structural formula is shown in Formula 2d, ([2-(benzothiazol-2-yl)phenyl] 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside).
  • 40
  • [ 95-16-9 ]
  • [ 90-02-8 ]
  • [ 3411-95-8 ]
YieldReaction ConditionsOperation in experiment
71% With tert.-butylhydroperoxide; N-chloro-succinimide In decane; dimethyl sulfoxide at 120℃; for 12h; Inert atmosphere;
71% With tert.-butylhydroperoxide; N-chloro-succinimide In decane; dimethyl sulfoxide at 120℃; for 10h; Schlenk technique; 16 Example 16 Synthesis of derivative Ip ((R) n = H, (R ’) m = 2-hydroxyl) Weigh 2-hydroxy-benzaldehyde (0.37 mmol, 45.5 mg) benzothiazole (1.0 eq., 0.37 mmol, 50.0 mg), NCS (30 mol%, 0.11 mmol, 14.7 mg) and 5.5 M TBHP in decane (1.5 eq., 0.37 mmol, 67 μL) in a 25 mL Schlenk reaction tube, then add DMSO (20 eq., 7.4 mmol, 0.58 g), and place the reaction at 120 ° C. After 12 h, the reaction is completed and the reaction solution is extracted with DCM The organic layer was concentrated to remove the solvent, and the concentrated solution was separated by column chromatography (eluent is a petroleum ether-ethyl acetate mixed solvent with a volume ratio of 1: 0.5) to obtain a white solid, namely the derivative Ip. The yield was 71%.
47% With di-tert-butyl peroxide In 1-methyl-pyrrolidin-2-one at 100℃; for 3h;
  • 41
  • [ 3411-95-8 ]
  • potassium trifluoro(methyl)boranuide [ No CAS ]
  • 2-(2-hydroxy-6-methylphenyl)-1,3-benzothiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(l) oxide In dichloromethane at 85℃; for 12h; 2 Example 2 The 2 - (2 - hydroxy) phenyl-benzothiazole (0.3mmol), methyl three fluoro potassium borate (0.9mmol, 3.0 equiv), oxidizing silver (0.3mmol, 1.0 equiv), catalyst dichloro (five methyl cyclopentadienyl) gathers the rhodium (III) dimer (0.012mmol, 0 . 04 equiv) and six fluorine stibium acid silver (0.048mmol, 0 . 16 equiv is dissolved in the organic solvent dichloromethane in, in 85 °C reaction air in under 12 hours, in the reaction process TLC detection to the complete response. Post-processing to add a little silica gel adsorption crude product and the solvent turns on lathe does, directly by silica gel column chromatography separation to obtain the 2 - (2 - hydroxy -6 - methyl) phenyl-benzothiazole compound 2b.Yield: 50%
50% With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(l) oxide In dichloromethane for 24h; Heating; Rhodium(III)-Catalyzed ortho-C-H Alkylation of 2-Arylbenzothi-azoles and 2-Arylthiazoles with Potassium Alkyltrifluoroborates;General Procedure General procedure: A suspension of the respective 2-arylbenzodthiazole 1 (0.2 mmol), alkylboron reagent 2 (0.6 mmol, 3.0 equiv), [RhCp * Cl2]2 (4.9 mg, 4 mol%), AgSbF6 (10.9 mg, 16 mol%), and Ag2O (46.3 mg, 1.0 equiv) in CH2Cl2 (2.0 mL) was stirred at 100 °C under air for 24 h. After the completion of the reaction (monitored by TLC), the solvent was concentrated in vacuo, and the residue was purified by flash column chromatography on silica gel with PE/EtOAc (30:1-20:1) as the eluent to give the desired product 3.
  • 42
  • [ 3411-95-8 ]
  • [ 2751-90-8 ]
  • C24H20P(1+)*C13H8NOS(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% 2- (2-hydroxyphenyl) benzothiazole (68.2 g, 0.3 mol) was added to 250 g of methanol and stirred to complete dissolution.NaOMe (Aldrich, 25 wt% in methanol) (64.8 g, 0.3 mol) was added thereto, followed by stirring at room temperature for 2 hours.Tetraphenyl phosphonium bromide (125.4 g, 0.3 mol) is added to the stirred solution and stirred for an additional 2 hours at room temperature.As the reaction proceeds, a little yellow precipitate is formed. The crude objective compound was obtained by reduced pressure filtration and further washed twice with 500 mL of water to obtain 139 g (yield: 82%) of the compound of the formula (1g) and confirmed by NMR data
  • 43
  • [ 3411-95-8 ]
  • [ 22883-70-1 ]
  • C24H20OP(1+)*C13H8NOS(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% Stage #1: 2-(benzothiazol-2-yl)phenol With sodium methylate In methanol at 20℃; for 2h; Stage #2: (4-hydroxy-phenyl)triphenylphosphonium bromide In methanol at 20℃; for 2h; 8 Preparation of a phosphonium-based compound represented by the formula (1h) 2- (2-hydroxyphenyl) benzothiazole (68.2 g, 0.3 mol) is added to 250 g of methanol and stirred to dissolve completely. NaOMe (Aldrich, 25 wt% in methanol) (64.8 g, 0.3 mol) was added thereto, followed by stirring at room temperature for 2 hours. Triphenyl-hydroxyphenyl phosphonium bromide (130.5 g, 0.3 mol) is added to the stirred solution and stirred for an additional 2 hours at room temperature.As the reaction proceeds, a little yellow precipitate is formed. The crude target compoundFiltered, and then washed twice with 500 mL of water to obtain 173 g (yield: 99%) of the compound of the formula (1c) and confirmed by NMR data
  • 44
  • [ 506-68-3 ]
  • [ 3411-95-8 ]
  • 12H-benzo[e]benzo[5,6][1,3]oxazino[2,3-c][1,2,4]thiadiazin-12-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
28.8% With triethylamine In tetrahydrofuran at 0 - 25℃; for 1h; Inert atmosphere; 2 Was added BrCN (157.5mg, 1.5mmol) added to the reaction flask, under nitrogen, was added 1ml of tetrahydrofuran at 0 . Compound 1a (120.5mg, 0.5mmol) dissolved in 2mL of tetrahydrofuran and 0.5mL of triethylamine was added the reaction flask, reaction at 25 deg.] C 1h. The reaction system by a simple column chromatography (eluent methylene chloride: petroleum ether = 1: 1) to give the desired product 20.7mg (0.074mmol). Yellow solid 2a, a yield of 14.8%.
28.7% With triethylamine In tetrahydrofuran at 0 - 20℃; for 0.5h; Inert atmosphere; General procedure for the preparation of 2a-j General procedure: A solution of BrCN (157.5 mg, 1.5 mmol) in 1 mL anhydrous THF was cooled to 0 °C (dry ice bath) under nitrogen atmosphere in a 10-mL bottle. Then, a solution of 1a-j (0.5 mmol) in 2 ml anhydrous THF and 10 dropwise NEt3 was added dropwise, and the resulting solution was stirred at room temperature for 0.5 h under the nitrogen atmosphere. Then, the solvent was evaporated to dryness. The residue was purified by column chromatography on silica gel to afford products 2a-j.
  • 45
  • [ 3411-95-8 ]
  • [ 761-65-9 ]
  • 2-(benzo[d]thiazol-2-yl)phenyl dibutylcarbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With tert.-butylhydroperoxide; copper ferrite In water at 100℃; for 2h;
64% With tert.-butylhydroperoxide; copper(II) ferrite In water for 2h; Heating; Catalytic studies The CuFe2O4 superparamagnetic nanoparticles were supplied by Sigma-Aldrich. The catalyst was subsequently characterized by various analytical protocols. In an representative experiment, 2-(2-hydroxyphenyl)benzothiazole (0.1136 g, 0.5 mmol) was dissolved in N,N’-dimethylformamide (DMF, 1.5 mL, 19 mmol), and the solution added into a 8 mL vial consisting of the pre-calculated quantity of catalyst. The catalyst amount was determined with respect to the copper/2-(benzo[d]thiazol-2-yl)phenol mole ratio. Subsequently, tert-butyl hydroperoxide (tBuOOH, 70% wt. in water; 0.0727 mL, 0.5 mmol) was added to the vial, and the resulting mixture magnetically stirred at 100 oC for 60 min under air. Next, the reactor was cooled to room temperature, and diphenyl ether (0.0851 g, 0.5 mmol) as an internal standard was added to the reaction mixture. Samples were taken, diluted with ethyl acetate (3 mL), stirred carefully with anhydrous Na2SO4 to remove water residue, and analyzed by GC regarding diphenyl ether internal standard. The o-(2-benzothiazolyl)phenyl dimethylcarbamate was purified using column chromatography and the product identity confirmed by GC-MS, 1H NMR and 13C NMR.
  • 46
  • [ 777-52-6 ]
  • [ 3411-95-8 ]
  • 2-(benzo[d]thiazol-2-yl)phenyl (4-nitrophenyl) phosphorochloridate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dimethyl piperazine; In tetrahydrofuran; at 0 - 50℃; for 5h; A solution of 2-(2-hydroxyphenyl)benzothiazole (3) (227 mg,1.0 mmo1) and dimethyl piperazine (DMPipz) (0.15 mL,1.1 mmo1) in THF (10 mL) was cooled to 0-5C. A solution of <strong>[777-52-6]4-nitrophenyl phosphorodichloridate</strong> (4) (256 mg, 1.0 mmol)in THF (5 mL) was added slowly to the above cold reaction mixture and vigorously agitated for 1.0 h at 5-10C. Then, the reaction mixture was heated to 45-50C slowly and stirred for 4.0 h.When TLC indicated the completion of reaction, the reaction was cooled to room temperature and filtered to remove the salt, DMPipz. HCl. The filtrate containing intermediate, 2-(benzo[d]thiazol-2-yl)phenyl (4-nitrophenyl) phosphorochloridate (5) was taken directly for the next step to prepare title products. To the filtrate having the intermediate 5, DMPipz (0.15 mL,1.1 mmol) followed by 1-(2-fluorophenyl)piperazine (6a)(180 mg, 1.0 mmol) were added at 10-20C. The reactionmixture temperature was raised to 45-50C and stirred for4.0 h. The progress of the reaction was monitored by TLC. The salt, DMPipz.HCl was removed by filtration. The filtrate was concentrated under vacuum to obtain the crude product, 2-(benzo[d]thiazol-2-yl) phenyl 4-nitrophenyl 4-(2-fluorophenyl)piperazin-1-ylphosphonate (7a).The compound was purified by column chromatography using ethyl acetate and n-hexane (2:3) as an eluent. The same experimental procedure was adopted for the synthesis of remaining title compounds (7b-j). Yields,reaction times and melting points of the title compounds are given along with spectral data. The numbering was given to the title compounds as shown in Figure-1B to characterize the compounds properly.
  • 47
  • [ 3411-95-8 ]
  • [ 6962-92-1 ]
  • C17H17NO2S [ No CAS ]
  • 48
  • [ 3411-95-8 ]
  • C24H51Cl3N3O9P3 [ No CAS ]
  • C63H75N6O12P3S3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
28% With sodium hydride In tetrahydrofuran at 20℃; for 120h; Inert atmosphere; 2.3.1 General procedure for compounds 4-6 General procedure: Compound 2 (0.5g, 0.69mmol) was dissolved in dry THF (tetrahydrofuran) (25mL) in a 100mL three-necked round-bottomed flask under an argon atmosphere. Dry THF solution (10mL) of thiazole [2-(2′-hydroxyphenyl)benzothiazole (0.47g, 2.07mmol)/4-methyl-5-thiazoleethanol (0.27g, 2.07mmol)/2-methyl-5-benzothiazolol (0.34g, 2.07mmol)] was added to the reaction mixture dropwise under an argon atmosphere and NaH (0.08g, 2.07mmol, 60%) was added to this mixture. The reaction mixture was stirred for five days in room temperature and followed by TLC, which indicated product formation. After the solution was filtered to remove sodium chloride salt, the solvent was removed under reduced pressure, using a rotary evaporator. The oily residue was purified using a column chromatography; Compound 4 (0.25g, 28%) was isolated by using hexane-THF (2/1) as a mobile phase. Calc. for C63H75N6O12P3S3 requires: C, 58.32; H, 5.83; N, 6.48%; M, 1297.42. Found: C, 57.84; H, 5.63; N, 6.57%; [M], 1297.10 m/z. Compound 5 (0.20g, 29%) was isolated by using THF-hexane (2/1) as a mobile phase. Calc. for C42H75N6O12P3S3 requires: C, 48.26; H, 7.23; N, 8.04%; M, 1045.19. Found for 5: C, 46.82; H, 7.35; N, 7.05%; [M+2H], 1047.04 m/z. Compound 6 (0.23g, 30%) was isolated by using ethyl acetate-hexane (3/1) as a mobile phase. Calc. for C48H69N6O12P3S3 requires: C, 51.88; H, 6.26; N, 7.56%; (M, 1111.21). Found for 6: C, 50.71; H, 7.07; N, 7.30%; [M], 1111.53 m/z.
  • 49
  • [ 3411-95-8 ]
  • C45H93Cl3N3O24P3 [ No CAS ]
  • C84H117N6O27P3S3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
28% With sodium hydride In tetrahydrofuran at 20℃; for 120h; Inert atmosphere; 2.3.2 General procedure for compounds 7-9 General procedure: Compound 3 (0.5g, 0.39mmol) was dissolved in dry THF (25mL) in a 100mL three-necked round-bottomed flask under an argon atmosphere. Dry THF solution (10mL) of thiazole [2-(2′-hydroxyphenyl)benzothiazole (0.26g, 1.17mmol)/4-methyl-5-thiazoleethanol (0.15g, 1.17mmol)/4-methyl-5-thiazoleethanol (0.15g, 1.17mmol)] was added to the reaction mixture dropwise under an argon atmosphere. NaH (0.05g, 1.17mmol, 60%) was added to reaction mixture. The reaction mixture was stirred for five days in room temperature and followed by TLC, which indicated product formation. After the solution was filtered to remove sodium chloride salt, the solvent was removed under reduced pressure, using a rotary evaporator. The oily residue was purified using a column chromatography; Compound 7 (0.20g, 28%) was isolated by using THF as the mobile phase. Calc. for C84H117N6O27P3S3 (for mPEG, n=7) requires: C, 55.07; H, 6.44; N, 4.59%; (M, 1830). Found for 6: C, 55.76; H, 6.90; N, 3.90%; [M], 1833.11 m/z. Compound 8 (0.25g, 41%) was isolated by using THF as the mobile phase. Calc. for C63H117N6O27P3S3 (for mPEG, n=7) requires: C, 47.90; H, 7.47; N, 5.32%; (M, 1578). Found for 8: C, 49.04; H, 8.44; N, 4.33%; [M], 1582 m/z. The compound 9 (0.21g, 32%) was isolated by using THF as the mobile phase. Calc. for C69H111N6O27P3S3 (for mPEG, n=7) requires: C, 50.36; H, 6.80; N, 5.11%; (M, 1644). Found for 8: C, 50.09; H, 7.11; N, 4.52%; [M], 1648 m/z.
  • 50
  • [ 670-96-2 ]
  • [ 14285-68-8 ]
  • [ 3411-95-8 ]
  • C25H16N3O4ReS [ No CAS ]
YieldReaction ConditionsOperation in experiment
31% In toluene; at 160℃; for 48.0h;High pressure; General procedure: <strong>[14285-68-8]Re2(CO)10</strong>, 2-(2′-hydroxyphenyl)-1H-benzimidazole (H2-PBI)/2-(2′-hydroxyphenyl) benzoxazole (H-PBO)/2-(2′-hydroxyphenyl)benzothiazole (H-PBT) and 2-phenylimidazole (ph-imz) in toluene (∼10mL) were kept in a Teflon vessel. The vessel was kept in the stainless steel solvothermal bomb and placed in an oven programmed at 160C for 48h and cooled to room temperature. Crystals or powder obtained in the bomb were filtered, washed with hexane, and air dried.
  • 51
  • [ 3411-95-8 ]
  • [ 7648-30-8 ]
  • [ 1454765-34-4 ]
YieldReaction ConditionsOperation in experiment
82% With potassium hydroxide In acetonitrile at 25℃; for 12h; 4.1. General procedure for difluoromethylation of 2-(2-hydroxyaryl)benzothiazoles 3 2-(o-Hydroxyphenyl)benzothiazoles were synthesized according to the reported procedures [16]. 2-(o-Hydroxyaryl)benzo[d]thiazole 1 (0.2 mmol), potassium hydroxide (6 equiv, 67.3 mg), acetonitrile (2 mL) and ethyl difluoroiodoacetate 2 (2.0 equiv, 100 mg) were continuously added to a 20 mL reaction tube. The reaction was stirred at 25 °C for 12 h. After completion of the reaction, it was detected by a TLC thin-layer silicagel plate, evaporation of the solvent under reduced pressure followed purification by silica gel chromatography using petroleum ether: ethyl acetate 50:1 as eluent to give 2-(o-difluoromethoxyphenyl)benzo[d]thiazole 3.4.2. Experimental data for compounds 3. 4.2.1. 2-(2-(Difluoromethoxy)phenyl)benzo[d]thiazole (3a) Colorless solid, 45.5 mg (82%), mp 51-53 °C. 1H NMR (400 MHz,CDCl3) δ 8.48 (dd, J 1.6, 7.6 Hz, 1H), 8.11 (d, J 8.0 Hz, 1H), 7.94 (d,J 7.6 Hz, 1H), 7.53-7.46 (m, 2H), 7.43-7.36 (m, 2H), 7.29 (d,J 8.4 Hz, 1H), 6.69 (t, J 73.2 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 161.9, 152.4, 148.8, 136.1, 131.6, 130.6, 126.2, 125.9, 125.7, 125.3, 123.3, 121.4, 119.6, 116.1 (t, 1JC-F 260 Hz). 19F NMR (376 MHz, CDCl3) δ 80.42. HRMS (ESI): m/z [M + H]+ calcd for C14H10F2NOS: 278.0446; found: 278.0450.
  • 52
  • [ 3411-95-8 ]
  • [ 100-97-0 ]
  • 3-(benzo[d]thiazol-2-yl)-2-hydroxybenzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% With trifluoroacetic acid for 6h; Reflux; 2.3. Synthesis of probe 1 The synthesis of compound 2 was based on the literature [50].Benzothiazole phenol (454 mg, 2 mmol) and hexamethylenetetramine(280 mg, 2 mmol) were dissolved into 10 mL TFA (trifluoroaceticacid). After reflux stirring for 6 h, the reaction mixture wascooled to room temperature, and adjusted pH to neutral withNaOH. A light yellow solid was obtained through filtration andwashed with saturated brine. The mixture was then decompressedand washed with saturated brine to produce a pale yellow solid.The crude products were purified by column chromatography onsilica gel (petroleum ether/ ethyl acetate = 5: 1) to obtain compound2 (326 mg, 64%).
50% With trifluoroacetic acid for 5h; Inert atmosphere; Schlenk technique; Reflux;
46% With trifluoroacetic acid at 80℃; for 9h; Cooling with ice; 2.5. Synthesize of 3-(benzo[d]thiazol-2-yl)-2-hydroxybenzaldehyde(HBT-CHO) HBT-CHO was synthesized according to Duff reaction. HBT (1.0 g,4.4 mmol) was added to 15 mL TFA solution cooled in ice-bath. HTMA(1.0 g, 7.1 mmol) was added to the solution in 30 min then heated up to80 for 9 h. Then 20 mL 4 N HCl was added to the solution refluxingfor 30 min. The hot solution was cooled to RT and extracted withdichloromethane (DCM). The organic layer was dried under vacuumafter treatment with anhydrous sodium sulphate to afford a yellow solid.The crude product was purified by column chromatography (silica gel,100-200 mesh, petroleum ether: ethyl acetate = 5:1, v/v) as yellowsolid (0.5 g, 46 % yield).
35% In trifluoroacetic acid
With trifluoroacetic acid
With trifluoroacetic acid at 75℃; for 6h; 1.1 Add 2mmol of benzothiazole phenol (454mg) and 2mmol of hexamethylenetetramine (280mg) in a 50mL round-bottomed flask, then dissolve them in 10mL of trifluoroacetic acid, in an oil bath at 75 Stir and reflux with a magnetic stirrer for 6 hours, cool to room temperature, adjust the pH to neutral with NaOH, filter under reduced pressure to obtain a light yellow solid, and continue to wash with saturated brine; the crude product is passed through silica gel column chromatography with a volume ratio of 10 1: Petroleum ether and ethyl acetate are used as eluents to obtain compound 2;

  • 53
  • [ 3411-95-8 ]
  • [ 94847-10-6 ]
  • 2-[2-(6-(9-carbazolyl)hexyl)phenyl]benzothiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With potassium carbonate; potassium iodide In N,N-dimethyl-d<SUB>6</SUB>-formamide at 20℃; for 24.5h; Inert atmosphere; Reflux; 1.3 Synthesis of 2- [2- (6- (9-carbazolyl) hexyl) phenyl] benzothiazole (CzhBTZ). Under nitrogen, 4 mmol BrCz and 5 mmol BTZ were added to a three-necked flask under a nitrogen atmosphere.In 30mL DMF, stir and mix well, add 2mol / L potassium carbonate solution, and then add an appropriate amount of potassium iodide, under a nitrogen atmosphereThe reaction was stirred at room temperature for 30 min, and heated at reflux for 24 h. After the reaction, the reaction solution was poured into ice water while hot, and white was precipitated.The color precipitate was filtered and dried. The white precipitate was recrystallized from dichloromethane to obtain CzhBTZ as a white solid with a yield of 72%.
  • 54
  • [ 3411-95-8 ]
  • [ 79-04-9 ]
  • chloro-acetic acid 2-benzothiazol-2-yl-phenyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% Stage #1: 2-(benzothiazol-2-yl)phenol With potassium carbonate In tetrahydrofuran for 0.5h; Stage #2: chloroacetyl chloride In tetrahydrofuran at 20 - 50℃; for 12h; 2.3. Synthesis of chloroacyl-2-hydroxy benzothiazole (HBT-AcCl) 2 In a 50 mL round bottom flask, 2-(2-hydroxyphenyl)-benzothiazole (227.14 mg,1 mmol)was stirred for 30 min with anhydrousK2CO3 (691 mg, 5 mmol) in dry THF (20 mL). Then, chloroacetylchloride (0.339 mL, 3 mmol) was added dropwise to the abovemixture. The reaction mixture was allowed to react at room temperaturefor 30 min and then heated to 50 C until the reactionwascompleted as monitored by TLC. After completion of the reaction in12 h, the solution was filtered to remove extra K2CO3. The filtratewas concentrated and dried by rotatory evaporator under reduced pressure wherein the solid product obtained was washed with dryhexane to give the pure off-white product in a 90% yield. Themelting point of product 2 was 110-112 C. 1H NMR (400 MHz,DMSO-d6) d: 8.19e8.17 (dd, J 7.89 Hz, 1H), 8.15e8.13 (d,J 7.91 Hz, 1H), 8.07e8.05 (d, J 8.12 Hz, 1H), 7.56e7.52 (t,J 7.64 Hz, 1H), 7.46e7.39 (m, 2H), 7.13e7.11 (dd, J 8.21 Hz, 1H),7.03e6.99 (t, J 12 Hz, 1H), 4.27 (s, 2H). 13C NMR (DMSO-d6,101 MHz): 168.64, 166.50, 162.17, 152.70, 147.56, 134.59, 132.38,130.15, 127.44, 126.84, 125.95, 124.11, 123.20, 122.25 and 41.62. ESIMS(positive mode, calculated [C15H10O2NSCl] is 303.01 and obtainedat 341.34 [C15H10O2NSClK].
  • 55
  • [ 3411-95-8 ]
  • [ 927-58-2 ]
  • [ 112-69-6 ]
  • C35H53N2O2S(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-(benzothiazol-2-yl)phenol; 4-bromobutyroyl chloride With piperidine In dichloromethane at 20℃; for 3h; Stage #2: N,N-dimethylhexadecylamine In tetrahydrofuran at 20℃; for 6h; 5 Example 5: (1) Dissolve 2.5 mmol 2-(2-hydroxyphenyl)benzothiazole and 7.5 mmol piperidine in 15 mL dichloromethane,Then add 3 mmol 4-bromobutyryl chloride dropwise and stir at room temperature for 3 h;After the reaction is completed, a petroleum ether/ethyl acetate system is used for column chromatography to obtain a white intermediate product;(2) Take 1 mmol of the white intermediate product obtained in step (1) and dissolve it in 20 mL of tetrahydrofuran,Then add 2 mmol of N,N-dimethylhexadecylamine dropwise, and stir for 6 h at room temperature;After the reaction, the pure quaternary ammonium salt probe compound is obtained by recrystallization.
  • 56
  • [ 3411-95-8 ]
  • [Pt(dmba)(DMSO)Cl] [ No CAS ]
  • C22H20N2OPtS [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% Stage #1: 2-(benzothiazol-2-yl)phenol With potassium hydroxide In methanol for 0.25h; Stage #2: [Pt(dmba)(DMSO)Cl] In methanol at 65℃; for 24h; 4.2. Preparation of monomeric Pt(II) compounds 1, 2 and 3 General procedure: The corresponding 2-benzoazole-phenol HLn (0.23 mmol) was treated with methanolic KOH (5 mL, 25.81 mg, 0.26 mmol) for15 min. The resulting solution was treated with a suspension of[Pt(dmba)(DMSO)Cl] (0.1 g, 0.23 mmol) in methanol (15 mL) atroom temperature for 48 h (for complexes 1 and 3) or for 24 h at65 C (complex 2). After removing solvent under reduced pressure,the residue was redissolved by the addition of CH2Cl2 (20 mL). Theresulting solution was filtered through Celite, and then the solventwas evaporated to dryness. The residue was treated with ether togive a precipitate that was filtered off and air-dried.
  • 57
  • [ 3411-95-8 ]
  • [ 13360-57-1 ]
  • 2-(benzo[d]thiazol-2-yl)phenyl dimethylsulfamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% Stage #1: 2-(benzothiazol-2-yl)phenol With sodium hydride In 1,2-dimethoxyethane at 0 - 20℃; for 0.166667h; Stage #2: dimethylamino sulfonyl chloride In 1,2-dimethoxyethane at 0 - 20℃; for 15h; Aryl Sulfamates 1; General Procedure General procedure: To a round-bottomed flask charged with NaH (60% in mineral oil, 480 mg, 12.0 mmol) was added a solution of the respective phenol (10.0mmol) in anhyd DME (12 mL) at 0 °C. The reaction mixture wasstirred at rt for 10 min. Dimethylsulfamoyl chloride (1.72 g, 12.0mmol) in anhyd DME (3 mL) was added at 0 °C, and the mixture wasallowed to stir at rt for 15 h. After the addition of H2O (10 mL), thesolvent was removed. The residue was dissolved in Et2O (10 mL) andwashed with aq 1 M KOH (15 mL) and H2O (10 mL). The combinedaqueous layers were extracted with Et2O (3 × 30 mL). The combinedorganic layers were washed with brine (10 mL), and dried (Na2SO4).Concentration and purification by silica gel column chromatographygave the desired product 1.Biphenyl-2,2′-diyl Bis(dimethylsulfamate) (1d)Prepared from 2,2′-dihydroxybiphenyl (559 mg, 3.0 mmol). Silica gelchromatography (hexane/EtOAc 3:1) gave a white solid; yield: 1.17 g(2.92 mmol, 97%); mp 137-139 °C; Rf = 0.11 (hexane/EtOAc 3:1).IR (ATR): 750, 840, 1190, 1360, 1500, 3070 cm-1.1H NMR (500 MHz, CDCl3): = 2.59 (s, 12 H), 7.33 (t, J = 8.1 Hz, 2 H),7.40-7.43 (m, 4 H), 7.56 (d, J = 8.1 Hz, 2 H).13C{1H} NMR (100 MHz, CDCl3): = 38.1 (CH3), 120.8 (CH), 126.1 (CH),129.5 (CH) 130.0 (C), 132.1 (CH), 147.8 (C).HRMS (FAB): m/z [M + H]+ calcd for C16H21N2O6S2: 401.0841; found:401.0841.
  • 58
  • [ 3411-95-8 ]
  • C7H2BrN3O [ No CAS ]
  • C20H10N4O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With sodium hydride In N,N-dimethyl-formamide; mineral oil at 60℃; for 12h; 3 Example 3 HBT (50.7 mg, 0.223 mmol) and cyano and bromobenzoxadiazole c (CBD-Br, 50.0 mg, 0.223 mmol) were dissolved in 4 mL of anhydrous DMF, and the strong base sodium hydrogen (content 60%) was dissolved in 4 mL of anhydrous DMF. ) 12 mg (0.30 mmol) was added to the mixture. The reaction was heated to 60°C and the reaction was stirred overnight for 12 hours. After cooling to room temperature, 25 mL of water was added to quench the reaction, then the reaction mixture was extracted with ethyl acetate (30 mL x 3), washed with water (30 mL x 2) and saturated brine (30 mL x 1), respectively,Finally dried over anhydrous Na2SO4. Purification by column chromatography gave fluorescent probe e (82.6 mg, 67%) as a white solid.
Same Skeleton Products
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