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CAS No. : | 92-85-3 | MDL No. : | MFCD00005065 |
Formula : | C12H8S2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GVIJJXMXTUZIOD-UHFFFAOYSA-N |
M.W : | 216.32 | Pubchem ID : | 7109 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 61.13 |
TPSA : | 50.6 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -4.45 cm/s |
Log Po/w (iLOGP) : | 2.66 |
Log Po/w (XLOGP3) : | 4.47 |
Log Po/w (WLOGP) : | 4.3 |
Log Po/w (MLOGP) : | 4.56 |
Log Po/w (SILICOS-IT) : | 4.14 |
Consensus Log Po/w : | 4.03 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.63 |
Solubility : | 0.00505 mg/ml ; 0.0000234 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -5.25 |
Solubility : | 0.00121 mg/ml ; 0.00000559 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -5.13 |
Solubility : | 0.00159 mg/ml ; 0.00000733 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 2.66 |
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: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | With aluminum (III) chloride; sulfur; In ligroin; at 80℃; for 5h; | The suspension of diphenyl sulfide (30.0 g, 0.16 mol) and aluminum chloride (21.0 g, 0.16 mol) in ligroin (100 mL) was heated at 80 C for 5 h. This reaction mixture was quenched with H2O and extract was dried up in vacuum after removal of the solvent. The residue was dissolve in CHCl3 and this suspension was filtered with Celite. Then, the solvent was evaporated and dried under vacuum and re-crystallization from CH2Cl2/hexane to give thianthrene 2 (15.0 g, 44%) as colorless crystals; mp 153-155 C (from CH2Cl2/hexane); 1H NMR (400 MHz, CDCl3) delta 7.20-7.25 (m, 4H), 7.45-7.50 (m, 4H); 13C NMR (100 MHz, CDCl3) delta 127.6, 128.7, 135.5; IR (KBr) 1558, 1540, 1433, 761 cm-1. HRMS (EI) calcd for C12H8S2: 216.0067; found: m/z 216.0061. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With nitric acid; In water; acetic acid; for 0.5h;Heating / reflux; | To a solution of thianthrene (10.0 g 46.2 mmole) in glacial acetic acid (160 mL), [HN03] (5.8 [ML)] in water (12.6 mL) was added through the top of the condenser. The color immediately changed to pink and eventually yellow. The reaction mixture was refluxed for an additional half hour and then poured into ice water (600 mL). White precipitate was formed and collected by filtration. The precipitate was redissolved in [CH2CK,] washed with water, and dried with [MGS04. THE] solvent was removed in vacuo to yield white powder (10.7 g, 95%) |
94% | With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0℃; for 1h;Inert atmosphere; | The starting material, thianthrene (10.0 g, 46.2 mmol) and CH 2 Cl 2 (150 ml) were added to the round bottom flask and purged with nitrogen, and mCPBA (8.7 g, 50.8 ml) was dissolved in CH 2 Cl 2 The solution is added dropwise and stirred for 1 hour. After the reaction is complete, the reaction mixture is extracted with aqueous NaHCO 3 and CH 2 Cl 2. Then, the organic layer was dried with MgSO 4 and concentrated to obtain 10.0 g of thianthrene 5-oxide (yield: 94%). |
93% | With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; for 1h;Cooling with ice; Inert atmosphere; | A soln of MCPBA (878 mg, 5.08 mmol) in CH2Cl2 (15 mL) was added to a stirred solution of thianthrene (1; 1.0 g, 4.62 mmol) in CH2Cl2 (15 mL) cooled in an ice bath under N2. After 1 h, the mixture was extracted with sat. aq NaHCO3 (3 × 15 mL). The organic layer was washed with H2O (2 × 25 mL) then dried (MgSO4) and concentrated under vacuum. The solid product was purified by TLC [silica gel, EtOAc-hexane (1:1)] to give colorless crystals; yield: 998 mg (93%); |
93% | With melamine-(H2SO4)3; C3H6N6*3HNO3; water; potassium bromide; In neat (no solvent); | General procedure: Melamine-(H2SO4)3 [(0.21 g, 0.5 mmol)] and melamine-(HNO3)3 [(0.16 g, 0.5 mmol)], KBr[(0.0095 g, 0.1 mmol)] and few drops of water were mixed with the substrate [Table 1, Entries12-21, (1 mmol)] and ground in a mortar and pestle for 5 min. The mixture was changed toa black paste. The completion of the reaction was monitored by TLC. Then the product wasextracted with boiling chloroform (2 × 10 mL) and dried with 5 g Na2SO4 and filtered off.CHCl3 was removed by simple distillation and crude products were obtained with high purity. |
92% | With dihydrogen peroxide; In neat (no solvent); at 20℃; for 1.16667h;Green chemistry; | General procedure: The sulfide (1mmol) was added to a mixture of 30% H2O2 (2.4 equiv, 1g) and MNPs-DABCO tribromide (10mg), and the mixture was stirred at room temperature for the time specified. The progress was monitored by TLC (EtOAc/n-hexane, 1/10). After completion of the reaction, the catalyst was separated from the product by an external magnet (within 5s) and the mixture was washed with Et2O (2×5mL) and decanted. The combined organics were dried over anhydrous Na2SO4 and then evaporation of diethyl ether under reduced pressure gave the pure products in 80-97% yields. |
92% | With 1,1?-(butane-1,4-diyl)bis(1,4-diazabicyclo[2.2.2]octane-1,4-diium) bis(hydrogen sulfate) dinitrate; potassium bromide; In neat (no solvent); at 20℃; for 0.5h;Green chemistry; | General procedure: A mixture of an sulfide (1 mmol), [C4(DABCO-H)2]·[HSO4]2[NO3]2(0.5 mmol) and KBr (0.05 mmol) was vigorously grind using a mortarand pestle at roomtemperature. After completion of the reaction (monitoredby TLC), 5 mL water was added to the mortar and the mixturewas filtered to separate the nitrated product. The products were purifiedwith short column chromatography. |
90% | With peracetic acid; In acetic acid; at 110 - 120℃; for 4h; | Thianthrene (5. 0G, 0. 023MOL) was added to acetic acid (40ML), stirred and heated to 110C- 120C until completely dissolved. An excess of peracetic acid (4. 4G, 0. 058MOL) was then added dropwise and the reaction mixture continuously stirred at this temperature for four hours. The reaction was followed using thin layer chromatography (TLC) using hexane: diethyl ether (80: 20 by volume) as an indication of thianthrene consumption because thianthrene and the sulphoxide have very distinct and separate spots/rf values. After cooling, the reaction mixture was poured into water (80ML), the resulting white precipitate filtered off, washed with water and dried in a vacuum oven at 50C for 4 hours. Product yield 4. 8g (90%) of white crystals. The product was analysed by IR, LCMS and HPLC. IR: 1078CM''AND 1029CM''S=0 due to sulphoxide. MS: MIT 233 (Mw of cation). HPLC: one very strong peak due to product, with a change in retention time and a shift in the characteristic chromophore compared to the starting material. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88.1% | With bromine; acetic acid; for 4h;Reflux; | In a round bottom flask thianthrene (95.0 g, 439 mmol), was stirred into 1520 mL of acetic acid and bromine (140.4 g, 878 mmol) was slowly added dropwise with stirring. Then the internal temperature of the flask was dropped to 80-90 C. After 4 hours of reflux, The reaction was terminated after about 70% by HPLC to ensure the completion and it was cooled to room temperature. To this, saturated aqueous solution of sodium thiosulfate was added and it was extracted with methylene chloride. The organic layer was concentrated under reduced pressure and crystallized with methanol to give <1-a> as a light brown solid 114.2g (88.1% yield). |
84% | With bromine; acetic acid; at 80℃; for 5h;Inert atmosphere; | Under nitrogen protection conditions,Weighed S18 (30mmol),Add 60mL of acetic acid,Under agitation,Add bromine (36 mmol) dropwise,The resulting mixed solution was stirred at 80 C for 5 h.The excess bromine was quenched with aqueous NaHSO3 and extracted with dichloromethane (100 mL×3).Collect organic phase,Drying with anhydrous Na2SO4. Filtration,The solvent was distilled off under reduced pressure using a rotary evaporator.The crude product was obtained.The crude product was purified by silica gel column chromatography eluting.Finally, it is purified by recrystallization from n-hexane to obtain a solid powder.S19 (25.2 mmol, 84%). |
84% | With bromine; acetic acid; In water; at 80℃; for 5h;Inert atmosphere; | Under nitrogen protection conditions, S17 (30 mmol) was weighed, 60 mL of acetic acid was added, 36 mmol of liquid bromine was added dropwise with stirring, and the resulting mixed solution was stirred at 80 C for 5 h.Quenching excess bromine with aqueous NaHSO3 solution,It was extracted with dichloromethane (100 mL × 3), and the organic phase was collected, dried over anhydrous Na2SO4, filtered, and evaporated.The crude product was purified by silica gel column chromatography eluting.Finally, it was purified by recrystallization from n-hexane to give solid powder S18 (25.2 mmol, 84%). |
84% | With bromine; acetic acid; at 80℃; for 5h;Inert atmosphere; | Under nitrogen protection conditions,Weighed S14 (30 mmol) and added 60 mL of acetic acid.Under stirring, 36 mmol of liquid bromine was added dropwise.The resulting mixed solution was stirred at 80 C for 5 h. Quenching excess bromine with aqueous NaHSO3 solution,Extract with dichloromethane (100 mL x 3) and collect the organic phase.Drying with anhydrous Na2SO4. After filtration, the solvent was distilled off under reduced pressure using a rotary evaporator.The crude product was obtained. The crude product was purified by silica gel column chromatography eluting.Finally, it was purified by recrystallization from n-hexane to obtain a solid powder S15.(25.2 mmol, 84%). |
84% | With bromine; acetic acid; at 80℃; for 5h;Inert atmosphere; | Under nitrogen protection conditions,Weigh S6 (30mmol),Add 60mL of acetic acid,Under agitation,36 mmol of liquid bromine was added dropwise, and the resulting mixed solution was stirred at 80 C for 5 h.The excess bromine was quenched with aqueous NaHSO3 and extracted with dichloromethane (100 mL×3). The organic phase was collected and dried over anhydrous Na2SO4.After filtration, the solvent was evaporated under reduced pressure using a rotary evaporator to give a crude material.The crude product was purified by silica gel column chromatography eluting.Finally, it was purified by recrystallization from n-hexane to give solid powder S7 (25.2 mmol, 84%). |
84% | With bromine; acetic acid; at 80℃; for 5h;Inert atmosphere; | Under nitrogen protection conditions, Weighed S8 (20mmol), Add 60mL of acetic acid, Under agitation, Add 24 mmol of liquid bromine dropwise, The resulting mixed solution was stirred at 80 C for 5 h. Quenching excess bromine with aqueous NaHSO3 solution, Extracted with dichloromethane (100 mL x 3), Collect organic phase, Drying with anhydrous Na2SO4. filter, The solvent was distilled off under reduced pressure using a rotary evaporator. The crude product was obtained. The crude product was purified by silica gel column chromatography gradient elution. Finally, it was purified by recrystallization from n-hexane to give solid powder S9 (16.8 mmol, 84%). |
84% | With bromine; acetic acid; at 80℃; for 5h;Inert atmosphere; | Under nitrogen protection, weighed S4 (30 mmol) and added 60 mL of acetic acid.Under stirring, 36 mmol of liquid bromine was added dropwise,The resulting mixed solution was stirred at 80 C for 5 h.The excess bromine was quenched with aqueous NaHSO3 and extracted with dichloromethane (100 mL×3).The organic phase was collected and dried over anhydrous Na 2SO 4. filter,The solvent was distilled off under reduced pressure using a rotary evaporator to give a crude material.The crude product was purified by silica gel column chromatography gradient elution.Finally recrystallization using n-hexanePurified to obtain a solid powderS5 (25.2 mmol, 84%). |
82.3% | With bromine; acetic acid; at 80℃; for 5h;Inert atmosphere; | thianthrene(4.34 g, 20 mmol) and acetic acid (40 mL) were added to a 250 mL two-necked flask and stirred. Under the protection of nitrogen,Add liquid bromine (3.84 g, 24 mmol) dropwise.Stirring was carried out at 80 C for 5 hours under reflux. When the reaction is over,Quenched with sodium bisulfite solution, and extracted with dichloromethane.The organic layer was dried with anhydrous magnesiumColumn chromatography (eluent is petroleum ether),Obtaining compound e 4.86g,The yield was 82.3%. |
77% | With N-Bromosuccinimide; dibenzoyl peroxide; In dichloromethane; at 20℃; for 5h;Inert atmosphere; | Under nitrogen, thianthrene 2.16g (10mmol), NBS (N-bromosuccinimide) 2.67g (15mmol) and BPO (benzoyl peroxide) 0.12g (0.5mmol) dissolved in CH2Cl was added, and stirred at room temperature for 5 hours. After the reaction was completed, sat NaHCO3 was added, and stirred for 30 minutes. Theorganic layer was extracted with MC, water in the reaction mixture was removed by drying with anhydrous MgSO4, and filtered under reduced pressure. The resulting product was concentrated by column with Hex: EA = 5: 1 and recrystallized to obtain intermediate L 2.27g (77%). |
60% | With bromine; acetic acid; at 80℃; for 4h;Inert atmosphere; | Br2 (0.3 mL, 4.85 mmol) was added dropwise to a stirred suspension of thianthrene 2 (509 mg, 2.35 mmol) in AcOH (10 mL) at rt under N2. After the addition was completed the mixture was allowed to warm to 80 C, and the resulted brown solution was stirred for 4 h. Then, the solvent was evaporated and dried in vacuo, the residue was chromatographed on silica gel using hexane and re-crystallized from hexane to give 2-bromothianthrene 6 as a colorless solid (416 mg, 60%); mp 87-89 C (from hexane); 1H NMR (400 MHz, CDCl3) delta 7.23-7.26 (m, 2H), 7.30-7.36 (m, 2H), 7.45-7.48 (m, 2H), 7.62 (d, J=2.0 Hz, 1H); 13C NMR (100 MHz, CDCl3) delta 121.4, 127.9, 127.9, 128.8, 128.8, 129.6, 130.6, 131.2, 134.7, 134.8, 135.2, 137.8; IR (KBr) 1420, 1070 cm-1. HRMS (EI) calcd for C12H7BrS2: 293.9173; found: m/z 293.9171. |
With bromine;iodine; trifluoroacetic acid; In dichloromethane; at 23℃; for 24h; | <strong>[92-85-3]<strong>[92-85-3]Thianthren</strong>e</strong> (21 g, VWR International) was placed in a 250 mL rb flask along with dichloromethane (DCM, 150 mL) and trifluoroacetic acid (TFAA, 6 mL). A small amount of iodine (0.4 g) was added, and bromine (19 g) was metered in. The reaction was allowed to proceed for 24 hours at +23C. It was then taken to rotary evaporator and DCM was removed at 45C/ 40 mbar and recycled (over 90%) for a new batch without reduction in yield. Toluene (100 mL) was added, and evaporation was continued until no vapors came out at 60C /15 mbar. A light red viscous material remained, which started crystallizing slowly upon cooling. | |
With bromine; acetic acid; at 80℃; for 5h;Inert atmosphere; | The thianthrene (5mmol, 1.08g)Add to a reaction flask containing 100 mL of acetic acid,Bromine (5 mmol, 800 mg) was added dropwise slowly.After passing nitrogen for 15 min, the reaction was heated at 80 C for 5 h.After the reaction is completed, the system is returned to room temperature, and the reaction is quenched by the addition of sodium hydrogen sulfite.Extracted with dichloromethane and saturated brine,The organic phase was recovered, and the solvent was evaporated under reduced pressure.The crude product was separated and purified by column chromatography. The eluent was petroleum ether/dichloromethane 5:1.The obtained intermediate was dried overnight and dissolved in 60 mL.Tetrahydrofuran in the reactor,Then 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (5 mmol, 0.82 mL) was added.N-butyllithium (4.5 mmol, 2 mL) was slowly added dropwise at -78 C.The reaction was carried out for 6 h to room temperature.The organic phase was extracted with dichloromethane and brine, and the solvent was evaporated under reduced pressure. The crude product is separated and purified by column chromatography.The eluent was petroleum ether/dichloromethane 2:1. The two-step yield was 65%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With calcium fluoride; dihydrogen peroxide; In neat (no solvent); at 80℃; for 1.33333h; | General procedure: A mixture of sulfide (1 mmol), 30% H2O2 (3.6 meq, 0.4 gr) and CaF2 (0.25 mmol, 0.019 g) was stirred at room temperature for the time specified in Table 2. The progress was monitored by TLC or GC. Crude sulfoxide was obtained after treating the reaction mixture with H2O (5 mL) and Et2O(35 mL) and substantial separation, washing with brine (15mL), drying over anhydrous Na2SO4 and evaporation of organicphase. If the product had purity below 90%, purification was performed using short column chromatography with EtOAc/n-hexane (1/10). All the products are known and were characterized by IR and 1H NMR and by melting point in comparison with those of authentic samples [2, 4, 7, 15]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetonitrile for 48h; also in the presence of 2,6-di-tert-butyl-4-methylpyridine (before, 1h after or 12 h after reaction had been started); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In benzene for 72h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetonitrile also in the presence of 2,6-di-tert-butyl-4-methylpyridine; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | To a stirred suspension of thianthrene (2.16 g, 10 mmol) in tetrahydrofuran at -78 C under an atmosphere of argon, n-butyllithium (9.4 ml, 15 mmol) was added dropwise. Then, the mixture was allowed to warm to room temperature and resulting was stirred for 30 min. After the solution was re-cooled to -78 C, dimethylformamide (2.3 ml, 30 mmol) was added. The reaction mixture was stirred at -78 C for 1 h and at room temperature for 2 h and then quenched with aqueous hydrochloric acid. Then, DCM was added, and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. After evaporating the solvent, the crude product was purified by silica gel column chromatography (eluent: ethyl acetate/light petroleum (1:9)), to give thianthrene-1-ylcarbaldehyde as a clear yellow oil (2.02 g, 83%). 1H NMR (400 MHz, CD2Cl2): delta 10.57 (s, 1H, HC]O), 7.83 (1H, dd, 2-H), 7.71 (1H, dd, 4-H), 7.49-7.59 (2H, m, AreH), 7.37 (1H, t, 3- H), 7.23-7.34 (2H, m, AreH). | |
78% | General procedure: The electrophile (0.55 mmol, 1.2 equiv) was added to the stirred solution of thianthren-1-yllithium (0.46 mmol, 1.0 equiv), prepared as described above, under N2 at -30 C, and the mixture was stirred for 2 h. The reaction was quenched with H2O (10 mL), and CHCl3 (20 mL) was added to the mixture. The organic layer was separated, washed successively with H2O (2 × 20 mL) and brine (2 × 20 mL), dried (MgSO4), and concentrated under vacuum gave a solid product that was purified by TLC. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 47.9 % Chromat. 2: 51.0 % Chromat. | With ammonia; sodium at -78℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 3.73 mg 2: 0.44 mg 3: 0.38 mg 4: 0.26 mg | With air at 900℃; Formation of xenobiotics; Further byproducts given. Title compound not separated from byproducts; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | Stage #1: Thianthrene With 4,4'-di-tert-butylbiphenyl; lithium In tetrahydrofuran at -90℃; for 0.75h; Stage #2: benzaldehyde In tetrahydrofuran at -90 - -70℃; for 0.75h; Stage #3: carbon dioxide In tetrahydrofuran at -70℃; for 0.25h; | |
58% | Stage #1: Thianthrene With 4,4'-di-tert-butylbiphenyl; lithium In tetrahydrofuran at -90℃; for 0.75h; Stage #2: benzaldehyde In tetrahydrofuran at -90℃; for 0.75h; Stage #3: carbon dioxide In tetrahydrofuran at -70℃; for 0.25h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 55 percent / lithium aluminium hydride, (2,2'-bipyridyl)(1,5-cyclooctadiene)nickel / tetrahydrofuran / 48 h / 55 °C 2: bromine / acetic acid 3: n-butyllithium / diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 55 percent / lithium aluminium hydride, (2,2'-bipyridyl)(1,5-cyclooctadiene)nickel / tetrahydrofuran / 48 h / 55 °C 2: bromine / acetic acid 3: n-butyllithium / diethyl ether 4: 82 percent / lithium aluminium hydride, (2,2'-bipyridyl)(1,5-cyclooctadiene)nickel / tetrahydrofuran / 48 h / 55 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With 1,10-Phenanthroline; potassium carbonate; sulfur; In dimethyl sulfoxide; at 90℃; for 12h; | The present invention is achieved in such a way that,To a 25 mL round bottom flask was added o-diiodobenzene (0.5 mmol)Sulfur powder (0.5 mmol),Cuprous iodide (0.05 mmol),1,10-phenanthroline (0.1 mmol),Potassium carbonate (1.0 mmol) andDimethyl sulfoxide (2 mL).The resulting mixture was stirred at 90 C for 12 hours.After cooling to room temperature, add 10 mL of water to the system,Then extracted with ethyl acetate (3 x 10 mL) and dried over anhydrous sodium sulfate. After the solvent was distilled off,The resulting residue was purified by silica gel column chromatography in 82% yield. |
68% | With 1,10-Phenanthroline; potassium carbonate; sulfur; copper(I) bromide; In dimethyl sulfoxide; at 90℃; for 24h;Inert atmosphere; | Under the protection of nitrogen, 8.3g (25.2mmol) o-diiodobenzene, 1.6g (50mmol) sulfur powder, 10.4g (75mmol) potassium carbonate, 0.36g (2.5mmol) copper bromide, 2.5g ( 12.5mmol)1,10-phenanthroline was added to a 100mL three-necked flask, 40mL of dimethyl sulfoxide was added thereto, and heated to 90 C with stirring for 24 hours,The temperature was lowered, the reaction was quenched with sodium thiosulfate solution, the reaction liquid was extracted with ethyl acetate several times, the organic phase was dried over magnesium sulfate and concentrated under reduced pressure,The resulting solid was purified by silica gel column chromatography using methylene chloride and n-heptane (1:10) to obtain compound 100-1 (3.7 g, yield 68%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | Stage #1: Thianthrene With n-butyllithium In tetrahydrofuran at -30℃; for 1h; Inert atmosphere; Reflux; Stage #2: N-Formylpiperidine In tetrahydrofuran at -30℃; for 2h; Inert atmosphere; | Substituted Thianthrenes 2 and 3; General Reaction12 General procedure: The electrophile (0.55 mmol, 1.2 equiv) was added to the stirred solution of thianthren-1-yllithium (0.46 mmol, 1.0 equiv), prepared as described above, under N2 at -30 °C, and the mixture was stirred for 2 h. The reaction was quenched with H2O (10 mL), and CHCl3 (20 mL) was added to the mixture. The organic layer was separated, washed successively with H2O (2 × 20 mL) and brine (2 × 20 mL), dried (MgSO4), and concentrated under vacuum gave a solid product that was purified by TLC. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With bis(methanesulfonyl)peroxide In acetonitrile at 29℃; for 3h; Sealed tube; | Representative procedure for the thianthrenation using dimesylperoxide Under an ambient atmosphere, a 50 ml round-bottom flask was charged with a Teflon-coated stir bar, thianthrene (0.865 g, 4.0 mmol, 1.0 equiv), methyl-2-methylbenzoate (0.665 g, 4.0 mmol, 1.0 equiv.), and acetonitrile (10 ml_). At room temperature (29 °C), tetrafluoroboric acid diethyl ether complex (1 .8 ml_, 13.2 mmol, 3.3 equiv) was added, followed by the slow addition of a solution of bis(methanesulfonyl) peroxide (0.837 g, 4.4 mmol, 1.1 equiv) in acetonitrile (10 ml_). After the addition of the bis(methanesulfonyl) peroxide, the reaction mixture became homogeneous and a deep blue color. The round-bottom flask was sealed with a septum and stirred at ambient temperature (29 °C) until methyl-2-benzoate was no longer visible by thin- layer chromatography (approx. 3 h). The reaction mixture was concentrated under reduced pressure, and taken up in methylene chloride (25 ml_). The organic phase washed three times with water, dried over sodium sulfate, and concentrated via rotary evaporator. The resulting foamy white solid was left overnight under high vacuum affording the title compound as a hygroscopic white solid (1 .51 g, 81 % yield).NMR Spectroscopy:1H NMR (500 MHz, Chloroform-d) d 8.53 - 8.46 (m, 2H), 7.80 - 7.66 (m, 6H), 7.58 (dd, J = 9.1 ,2.5 Hz, 1 H), 7.48 (d, J = 2.8 Hz, 1 H), 7.05 (d, J = 9.2 Hz, 1 H), 3.84 (s, 3H), 3.75 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 1.48 g 2: 1.71 g | With palladium diacetate; sodium pivalate; XPhos In dichloromethane; acetone at 20℃; for 21h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: dichloromethane / 1.5 h / -40 - 20 °C / Schlenk technique; Inert atmosphere 2: palladium diacetate; XPhos; sodium pivalate / acetone; dichloromethane / 21 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | With trifluoroacetic anhydride In acetonitrile at -78 - 25℃; for 3h; Sealed tube; | A 20 ml glass-vial was charged with clozapine (0.20 mg, 0.61 mmol), and MeCN (5 ml).After cooling to -78 °C, trifluoroacetic anhydride (0.19 ml, 1.4 mmol) was added to the frozen thereaction mixture. Thianthrene (4 mg, 19 μmol), thianthrene-S-oxide (138 mg, 0.59 mmol) wereadded, followed by the addition of triflic acid (230 μl, 2.6 mmol, 4.2 equiv.) in one portion at -78 °C. The vial was sealed with a screw-cap, and the mixture was allowed to stand at -78 °C for1.5 hours, followed by warming the reaction mixture to 25 °C over a period of 1.5 hours. Thereaction mixture was concentrated under reduced pressure and dissolved in DCM (10 ml) followedby addition of saturated aqueous NaHCO3 solution (10 ml). The organic layers were separated,and the aqueous layer was extracted into DCM (2 x 10 mL). The DCM fractions were combined, dried over MgSO4, filtered, and the solvent was removed under reduced pressure. The cruderesidue was purified by silica gel chromatography (0→100% MeOH/DCM) to provide 143 mg(43% yield) of S004 as a white solid. |
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