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[ CAS No. 15864-32-1 ] {[proInfo.proName]}

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Chemical Structure| 15864-32-1
Chemical Structure| 15864-32-1
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Product Details of [ 15864-32-1 ]

CAS No. :15864-32-1 MDL No. :MFCD00152229
Formula : C7H5BrN2S Boiling Point : -
Linear Structure Formula :- InChI Key :VZEBSJIOUMDNLY-UHFFFAOYSA-N
M.W : 229.10 Pubchem ID :85149
Synonyms :

Calculated chemistry of [ 15864-32-1 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 51.72
TPSA : 67.15 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.82 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.95
Log Po/w (XLOGP3) : 2.65
Log Po/w (WLOGP) : 2.65
Log Po/w (MLOGP) : 2.01
Log Po/w (SILICOS-IT) : 3.1
Consensus Log Po/w : 2.47

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.54
Solubility : 0.0668 mg/ml ; 0.000292 mol/l
Class : Soluble
Log S (Ali) : -3.71
Solubility : 0.0445 mg/ml ; 0.000194 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.47
Solubility : 0.0776 mg/ml ; 0.000339 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.11

Safety of [ 15864-32-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H317-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 15864-32-1 ]

* 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.

  • Upstream synthesis route of [ 15864-32-1 ]
  • Downstream synthetic route of [ 15864-32-1 ]

[ 15864-32-1 ] Synthesis Path-Upstream   1~22

  • 1
  • [ 15864-32-1 ]
  • [ 53218-26-1 ]
YieldReaction ConditionsOperation in experiment
79% With silver(I) nitrite In 1,2-dichloro-ethane at 80℃; for 72 h; Sealed tube It was added in a closed reaction vessel 0.3mmol2-amino-6-bromo thiazole, 0.9mmol silver nitrite, 3mL1,2-dichloroethane, the reaction mixture was stirred at the reaction condition of80 72 hours. After the reaction was stopped, cooled to room temperature, thereaction mixture was added 10mL diluted with dichloromethane, filtration andstripped of solvent under reduced pressure, the residue was purified by columnchromatography, eluent V (petroleum ether) / V (ethyl ester) = 6/1, to give6-chlorobenzothiazole, yield 79percent.
Reference: [1] Patent: CN105367442, 2016, A, . Location in patent: Paragraph 0019
[2] Organic Letters, 2013, vol. 15, # 17, p. 4600 - 4603
[3] Tetrahedron, 2014, vol. 70, # 2, p. 245 - 250
  • 2
  • [ 15864-32-1 ]
  • [ 80945-86-4 ]
YieldReaction ConditionsOperation in experiment
53.7% With copper dichloride; isopentyl nitrite In tetrahydrofuran; acetonitrile at 65 - 85℃; for 1.5 h; Iso-Pentyl nitrite (0.9 mL, 6.8 mmol) and copper (II) chloride (0.938 g, 5.5 mmol) were suspended in CH3CN (25 mL), and the mixture was stirred at 65° C. for 30 min. A solution of 6-bromobenzo[d]thiazol-2-amine (I-2) (1 g, 4.37 mmol) in THF (20 mL) was added dropwise, and the resulting mixture was stirred at 85° C. for 1 h. The mixture was allowed to cool to RT, poured into 20percent HCl (200 mL), filtered, and the cake was washed with water (50 mL). The crude product was purified by flash column chromatography on silica gel (200-300 mesh) eluting with petroether/ethyl acetate (40/1) to give the desired product, 6-bromo-2-chlorobenzo[d]thiazole (701) (0.58 g, 53.7percent yield) as a pale solid. ESI-MS (M+H)+m/z: 247.9.
Reference: [1] Patent: US2015/225407, 2015, A1, . Location in patent: Paragraph 0416
[2] Journal of the Chemical Society, 1930, p. 2190,2209
[3] Journal of the Indian Chemical Society, 1933, vol. 10, p. 563,568
[4] Farmaco, 1994, vol. 49, # 3, p. 153 - 166
[5] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 14, p. 4022 - 4025
  • 3
  • [ 333-20-0 ]
  • [ 106-40-1 ]
  • [ 15864-32-1 ]
YieldReaction ConditionsOperation in experiment
93%
Stage #1: With nano-BF3/SiO2 In acetonitrile for 0.5 h; Cooling with ice
Stage #2: With bromine In acetonitrile at 0 - 20℃; for 5 h;
A solution of substituted aniline (2 mmol) in acetonitrile (15 ml) was added to a solution of KSCN (8 mmol) in acetonitrile (15 ml). Then, 0.06 g (30 mol percent BF3) of nano-BF3/SiO2 was added to the mixture, then was placed in a freezing mixture of ice and salt and mechanically stirred for 30 min. Then, bromine (4 mmol, 0.2 ml) in acetonitrile (3 ml) as solvent was added from a dropping funnel at such a rate that the temperature never rose beyond 0°C. After all the bromine was added at 60 min, the solution was stirred for 4 h at room temperature. The progress of the reaction was monitored by TLC. Then, the mixture was poured into water with stirring and the mixture was heated to 70°C on a steam bath and filtered hot to remove the catalyst and the recovered catalyst was washed with acetone and reused in the reaction. The filtrate was neutralized with 10 percent NaOH solution and the precipitate was collected on a filter, dried and recrystallized from ethanol (10 ml) to afford the corresponding products. All of the 2-aminobenzothiazole products were identified by physical and spectroscopic data as reported below, compared and contrasted with authentic samples. Spectral data for selected products 6-Bromo-1,3-benzothiazol-2-amine (2e) Yellow solid; Yield = 93 percent; m.p. =202–204°C; (m.p. = 203°C), FT-IR (KBr)/t(cm-1): 3315, 3012, 2835,1580, 1476, 1261, 920, 742, 512. 1H NMR (400 MHz, CDCl3)/d ppm: 5.44 (s, 2H, NH2) 7.4–7.5 (d, 2H, Ar–H), 7.71 (s, 1H, Ar–H); 13C NMR/(100 MHz, DMSO-d6)/d ppm: 119, 120.9, 125.15, 126.07, 133.1, 152.15, 167.75.
79%
Stage #1: at 20℃; for 1.33333 h; Inert atmosphere
A solution of 4-bromoaniline (0.500 g, 2.91 mmol) and potassium thiocyanate (1.13 g, 11.6 mmol) in AcOH (10 ml) was stirred at 20 °C for 10 min. Bromine (150 μl, 2.91 mmol) was added over 20 min to the above solution. The reaction mixture was stirred further at room temperature for 60 min. On completion of reaction following a TLC examination, the reaction mixture was poured into a solution of NH3 5M and extracted with AcOEt. The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product obtained was purified by flash chromatography (Hex:AcOEt 1:1) to afford 1e as white solid (2.67 g, yield 79percent). 1H NMR (DMSO-d6, 400 MHz): δ 7.91 (1H, d, J = 2.5 Hz), 7.63 (2H, s), 7.35 (1H, dd, J = 11.6, 2.5 Hz), 7.26 (1H, d, J = 11.6 Hz). MS-EI m/z [M]+ 228.
76%
Stage #1: at 20℃; Cooling with ice
Stage #2: With ammonium hydroxide In water
General procedure: A mixture of 0.1 mol of 4-substituted aniline and 0.1 mol of Potassium thiocyanate (KCNS) in 100 ml glacial acetic acid (AcOH) was cooled in an ice bath and stirred for 10-20 min, and then 0.1 mol bromine in glacial acetic acid was added dropwise at such a rate to keep the temperature below 10 °C throughout the addition. The reaction mixture was stirred at room temperature for 2-4 h, the hydrobromide (HBr) salt thus separated out was filtered, washed with acetic acid, dried, dissolved in hot water and basified to pH 11.0 with ammonia solution (NH4OH) and the resulting precipitate was filtered, washed with water and dried to get the desired product 3a-k. The progress of the reaction was monitored by Thin Layer Chromatography using toluene: acetone (8:2) solvent system.
76% With bromine In acetic acidCooling with ice General procedure: A mixture of 0.1 mol of 4–substituted aniline and 0.1 mol ofPotassium thiocyanate (KCNS) in 100 ml glacial acetic acid (AcOH) was cooled inan ice bath and stirred for 10 to 20 min, and then 0.1 mol bromine in glacialacetic acid was added dropwise at such a rate to keep the temperature below 10C throughout the addition. Theprogress of the reaction was monitored by Thin Layer Chromatography usingtoluene: acetone (8:2) solvent system. The reaction mixture was stirredat room temperature for 2 to 4 hrs, the hydrobromide (HBr) salt thus separatedout was filtered, washed with acetic acid, dried, dissolved in hot water and basified to pH 11.0 with ammonia solution (NH4OH)and the resulting precipitate was filtered, washed with water and dried to getthe desired product 2a-q.
72.3%
Stage #1: at -10 - 20℃; for 12.5 h;
Stage #2: With ammonium hydroxide In waterHeating
General procedure: An appropriately p-substituted aniline (0.1 mol) and potassiumthiocyanate (KCNS, 9.718 g, 0.1 mol) were dissolvedin 100 mL of glacial acetic acid (AcOH), cooled inice–salt mixture and stirred mechanically, while a solutionof bromine (15.980 g, 0.1 mol) in AcOH (20 mL)was slowly added drop by drop (Palkar et al. 2010).External cooling was applied throughout the process to keepthe temperature below 10 °C and the stirring was continuedfor 30 min. After all of the bromine had been added, thesolution was stirred for 2 h below room temperature and atroom temperature for 10 h. It was then allowed to standovernight during which the precipitate of imino-benzo[d]thiazole hydrobromide salt thus separated out was filtered,washed with acetic acid, dried, dissolved in hot water andbasified to pH 11.0 with ammonia solution (NH4OH) andthe resulting precipitate was filtered, washed with water anddried to get the desired products 2-amino-6-substitutedbenzo[d]thiazole (1a–d). The progress of the reaction wasmonitored by TLC using acetone (20percent) in toluene solvent.
65.5% at 25 - 35℃; for 20 h; General procedure: A solution of bromine (0.26mL, 10.0mmol) in acetic acid (5.0mL)was added over about 30 min to a mixture of aromatic amine(10.0 mmol) and potassium thiocyanate (1.07 g, 11.0 mmol) in aceticacid (20 mL), the temperature being kept between 25 and 35 °C. The slurry was then stirred for 20 h at room temperature. The precipitate was filtered, washed with a little acetic acid, slurried in water, made neutral with aqueous ammonia, and filtered again. The residue was boiled for 20 min with excess of hydrochloric acid (15percent v:v) and the hot mixture was filtered from impurities. The filtrate, cooled to 10 °C,was made alkaline with aqueous ammonia and the precipitate was filtered,washed, and dried. The crude product was recrystallized from ethanol–water to afford I–IV, respectively.
49% With N-Bromosuccinimide; acetic acid In tetrahydrofuran at -30 - 20℃; 4-Bromoaniline (I−1) (120 g, 0.697 mol) and KSCN (69 g, 0.697 mol) were dissolved in a mixture of THF (500 mL) and AcOH (450 mL). The mixture was stirred at RT for 30 min. and then was cooled to −30° C., solid NBS (124 g, 0.697 mol) was added slowly. The resulting mixture was stirred at −30° C. for 30 min., and then was allowed to warm to RT and stirred overnight. The solution was poured into stirred ice-water (3000 mL), ammonia solution was added to adjust the pH value to 9 and then filtered. The filtrate was extracted with ethyl acetate (2000 mL), washed with water (500 mL), dried over Na2SO4 and filtered. The filtrate was heated to reflux for 20 min., and then cooled to 0° C. The mixture was filtered through silica gel (10 g), and the filtrate was concentrated in vacuo. The crude product was taken in chloroform (1500 mL), heated to reflux for 30 min., and then cooled to 0° C. The precipitate was collected by filtration and further dried in vacuo to afford the desired product, 6-bromobenzo[d]thiazol-2-amine I-2 (78 g, 49percent yield) as a white solid. ESI-MS (M+H)+m/z: 230.90

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  • 5
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  • 6
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  • 7
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YieldReaction ConditionsOperation in experiment
77%
Stage #1: at 10℃;
Stage #2: at 10 - 20℃; for 4 h;
General procedure: A mixture of aniline (0.05mol) and NH4SCN (19.03g, 0.25mol) in glacial acetic acid (100mL) was cooled to 10°C in an ice bath and stirred for 10–20min. Then bromine (2.82mL, 0.055mol) in glacial acetic acid was added drop wise at such a rate to keep the temperature below 10°C. The mixture was stirred at room temperature for 4h and then poured into hot water (500mL), and basified to pH 11.0 with ammonia solution (NH4OH). The resulting precipitate was filtered, washed with water and dried to get a light yellow to brown solid. The crude product was purified by chromatography on silica gel using MeOH/CH2Cl2 to afford compounds 2a–2k in good yields.
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