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CAS No. : | 103261-70-7 | MDL No. : | MFCD13176733 |
Formula : | C10H9NO2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZSBYCGYHRQGYNA-UHFFFAOYSA-N |
M.W : | 207.25 | Pubchem ID : | 10608408 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.2 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 55.71 |
TPSA : | 67.43 Ų |
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) : | -5.72 cm/s |
Log Po/w (iLOGP) : | 2.05 |
Log Po/w (XLOGP3) : | 2.6 |
Log Po/w (WLOGP) : | 2.47 |
Log Po/w (MLOGP) : | 1.65 |
Log Po/w (SILICOS-IT) : | 3.29 |
Consensus Log Po/w : | 2.41 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.04 |
Solubility : | 0.189 mg/ml ; 0.000911 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.67 |
Solubility : | 0.0448 mg/ml ; 0.000216 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.46 |
Solubility : | 0.0724 mg/ml ; 0.000349 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.03 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
94% | With sodium hydroxide In tetrahydrofuran; methanol; water at 20℃; for 18 h; | To a solution of ethyl 1,3-benzothiazole-5-carboxylate (5.30 g, 25.6 mmol) in a mixture of methanol (150 mL), tetrahydrofuran (40 mL) and water (5 mL) was added a 50percent aqueous solution of sodium hydroxide (10 mL). The mixture was maintained at rt for 18 h and was concentrated. The residue was partitioned between water (300 mL) and diethyl ether (200 mL) and the organic layer was removed. Concentrated hydrochloric acid was added to the aqueous layer to adjust the pH to 4 and the mixture was extracted with ethyl acetate (3 x 300 mL). The combined extracts were washed with brine (200 mL), dried over anhydrous sodium sulfate, and concentrated to yield 4.30 g (94percent) the acid. |
94% | Stage #1: With sodium hydroxide; water In tetrahydrofuran; methanol at 20℃; for 18 h; Stage #2: With hydrogenchloride In water |
To a solution of 4-chloro-3-nitrobenzoic acid (99.2 mmol) in N, N-dimethylformamide (400 mL) was added potassium carbonate (254 mmol). After 30 min, ethyl iodide (119 mmol) was added and the reaction mixture was heated at 50 °C for 4 h. Water (3 L) was added and the mixture was extracted with diethyl ether (2 x 500 mL). The organic extracts were combined, washed with brine (1 L), dried over anhydrous sodium sulfate and concentrated. The residue was crystallized from hexanes, thus providing the ester in 86percent yield.'H NMR (500 MHz, CDC13) 8 8. 51 (d, 1H), 8.17 (dd, 1H), 7.65 (d, 1H), 4.43 (q, 2H), 1.42 (t, 3H). Sulfur (49.91 mmol) was dissolved in a solution of sodium sulfide nonahydrate (49.96 mmol) in water (60 mL). This solution was combined with a solution of ethyl 4-chloro- 3-nitrobenzoate (85.36 mmol) in ethanol (100 mL) and the resulting mixture was heated at reflux for 3 h. The hot reaction mixture was poured into water (600 mL) and maintained for 15 min. The product was isolated by filtration and recrystallized from ethanol, thus providing the disulfide in 77percent yield. 1H NMR (500 MHz, CDC13) 8 8.96 (d, 1H), 8.19 (dd, 1H), 7.88 (d, 1H), 4.43 (q, 2H), 1.41 (t, 3H). A mixture of diethyl 4,4'-dithiobis (3-nitrobenzoate) (24.8 mmol) and zinc granules (234 mmol) in formic acid (600 mL) was heated to reflux for 48 h. The mixture was allowed to cool to room temperature and concentrated to dryness. The residue was partitioned between ethyl acetate (500 mL) and saturated aqueous sodium bicarbonate (500 mL). The organic layer was separated, dried over anhydrous sodium sulfate and concentrated. The residue was chromatographed on neutral Alumina (1/1 to 0/1 hexanes/dichloromethane), thus providing the thiazole in 51percent yields NMR (500 MHz, CDCl3) 5 9. 08 (s, 1H), 8.83 (d, 1H), 8.14 (dd, 1H), 8.02 (d, 1H), 4.45 (q, 2H), 1.44 (t, 3H); MS (EI) nilz 208 (M++1). To a solution of ethyl 1, 3-benzothiazole-5-carboxylate (25.6 mmol) in a mixture of methanol (150 mL), tetrahydrofuran (40 mL) and water (5 mL) was added a 50percent aqueous solution of sodium hydroxide (10 mL). The mixture was maintained at rt for 18 h and was concentrated. The residue was partitioned between water (300 mL) and diethyl ether (200 mL) and the organic layer was removed. Concentrated hydrochloric acid was added to the aqueous layer to adjust the pH to 4 and the mixture was extracted with ethyl acetate (3 x 300 mL). The combined extracts were washed with brine (200 mL), dried over anhydrous sodium sulfate, and concentrated thus providing the acid in 94percent yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | With formic acid; zinc In formic acid for 48 h; Heating / reflux | A mixture of diethyl 4,4'-dithiobis (3-nitrobenzoate) (11.2 g, 24.8 mmol) and zinc granules (15.0 g, 234 mmol, 9.5 eq) in formic acid (600 mL) was heated to reflux for 48 h. The mixture was allowed to cool to room temperature and concentrated to dryness. The residue was partitioned between ethyl acetate (500 mL) and saturated aqueous sodium bicarbonate (500 mL). The organic layer was separated, dried over anhydrous sodium sulfate and concentrated. The residue was chromatographed on neutral Alumina (1/1 to 0/1 hexanes/dichloromethane) to provide 5.30 g (51 percent) of the benzthiazole. 1H NMR (500 MHz, CDCl3) delta; 9.08 (s, 1H), 8.83 (d, 1H), 8.14 (dd, 1H), 8.02 (d, 1H), 4.45 (q, 2H), 1.44 (t, 3H); MS (EI) m/z 208 (M+ +1). |
51% | With zinc In formic acid for 48 h; Heating / reflux | To a solution of 4-chloro-3-nitrobenzoic acid (99.2 mmol) in N, N-dimethylformamide (400 mL) was added potassium carbonate (254 mmol). After 30 min, ethyl iodide (119 mmol) was added and the reaction mixture was heated at 50 °C for 4 h. Water (3 L) was added and the mixture was extracted with diethyl ether (2 x 500 mL). The organic extracts were combined, washed with brine (1 L), dried over anhydrous sodium sulfate and concentrated. The residue was crystallized from hexanes, thus providing the ester in 86percent yield.'H NMR (500 MHz, CDC13) 8 8. 51 (d, 1H), 8.17 (dd, 1H), 7.65 (d, 1H), 4.43 (q, 2H), 1.42 (t, 3H). Sulfur (49.91 mmol) was dissolved in a solution of sodium sulfide nonahydrate (49.96 mmol) in water (60 mL). This solution was combined with a solution of ethyl 4-chloro- 3-nitrobenzoate (85.36 mmol) in ethanol (100 mL) and the resulting mixture was heated at reflux for 3 h. The hot reaction mixture was poured into water (600 mL) and maintained for 15 min. The product was isolated by filtration and recrystallized from ethanol, thus providing the disulfide in 77percent yield. 1H NMR (500 MHz, CDC13) 8 8.96 (d, 1H), 8.19 (dd, 1H), 7.88 (d, 1H), 4.43 (q, 2H), 1.41 (t, 3H). A mixture of diethyl 4,4'-dithiobis (3-nitrobenzoate) (24.8 mmol) and zinc granules (234 mmol) in formic acid (600 mL) was heated to reflux for 48 h. The mixture was allowed to cool to room temperature and concentrated to dryness. The residue was partitioned between ethyl acetate (500 mL) and saturated aqueous sodium bicarbonate (500 mL). The organic layer was separated, dried over anhydrous sodium sulfate and concentrated. The residue was chromatographed on neutral Alumina (1/1 to 0/1 hexanes/dichloromethane), thus providing the thiazole in 51percent yields NMR (500 MHz, CDCl3) 5 9. 08 (s, 1H), 8.83 (d, 1H), 8.14 (dd, 1H), 8.02 (d, 1H), 4.45 (q, 2H), 1.44 (t, 3H); MS (EI) nilz 208 (M++1). To a solution of ethyl 1, 3-benzothiazole-5-carboxylate (25.6 mmol) in a mixture of methanol (150 mL), tetrahydrofuran (40 mL) and water (5 mL) was added a 50percent aqueous solution of sodium hydroxide (10 mL). The mixture was maintained at rt for 18 h and was concentrated. The residue was partitioned between water (300 mL) and diethyl ether (200 mL) and the organic layer was removed. Concentrated hydrochloric acid was added to the aqueous layer to adjust the pH to 4 and the mixture was extracted with ethyl acetate (3 x 300 mL). The combined extracts were washed with brine (200 mL), dried over anhydrous sodium sulfate, and concentrated thus providing the acid in 94percent yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | for 48 h; Heating / reflux | Aldehyde preparation: To a solution of 4-chloro-3-nitrobeznoic acid (20 g, 99.2 mmol, 1.0 eq) in dimethylformamide (400 mL) was added potassium carbonate (35 g, 254 mmol, 2.55 eq). The mixture was stirred 30 min and ethyl iodide (18.6 g, 119 mmol, 1.20 eq) was added. The reaction mixture was stirred at 50 [°C] for 4h. Water (3 L) was added and the mixture was extracted with diethyl ether (2 x 500 mL). The organic extracts were combined, washed with brine (1 L), dried over anhydrous sodium sulfate and concentrated. The residue was crystallized from hexanes to provide 19.7 g (86percent) of the ester. Data [: IH] NMR (500 MHz, CDC13) [8] 8.51 (d, 1H), 8.17 (dd, 1H), 7.65 (d, 1H), 4.43 (q, 2H), 1.42 (t, 3H). Sulfur (1.60 g, 49.9 mmol, 0.58 eq) was dissolved in a solution of sodium sulfide [NONAHYDRATE] (12.0 g, 50.0 mmol, 0.58 eq) in water (60 [ML).] This solution was combined with a solution of ethyl 4-chloro-3-nitrobenzoate (19.6 g, 85.4 mmol, 1.00 eq) in ethanol (100 mL). The resulting mixture was heated at reflux for 3 h. The hot reaction mixture was poured into water (600 mL) and stirred for 15 min. The product was isolated by filtration and recrystallized from ethanol to provide 16.45 g (77percent) of the disulfide. Data: [APOS;H NMR] (500 MHz, CDC13) [5] 8.96 (d, 1H), 8.19 (dd, 1H), 7.88 (d, 1H), 4.43 (q, 2H), 1.41 (t, 3H). A mixture of diethyl 4,4'-dithiobis (3-nitrobenzoate) (11.2 g, 24.75 mmol, 1.00 eq) and zinc granules (15.0 g, 234 mmol, 9.47 eq) in formic acid (600 mL) was heated to reflux for 48 h. The mixture was cooled to room temperature and concentrated to dryness on vacuum rotary evaporator. The residue was partitioned between ethyl acetate (500 mL) and saturated aqueous sodium bicarbonate (500 mL). The organic layer was separated, dried over anhydrous sodium sulfate and concentrated on vacuum rotary evaporator. The residue was purified by chromatography on neutral Alumina (1/0 to 0/1 hexanes/dichloromethane) to provide 5.30 g (51percent) of the benzthiazole ester. Data: 1H NMR (500 MHz, [CDC13)] [8] [9. 08 (S, 1H),] 8.83 (d, 1H), 8.14 (dd, 1H), 8.02 (d, 1H), 4.45 (q, 2H), 1.44 (t, 3H); MS [(EI)] m/z 208 [(M++1).] Diisobutylaluminum hydride (1.0 M in dichloromethane, 6.0 mL, 6 mmol, 1.05 eq) was added over 15 min to a solution of the ester (1.18 g, 5.70 mmol) in dichloromethane (40 mL) [AT-35] [°C.] The reaction mixture was allowed to warm to rt and was maintained overnight. Analysis of the reaction progress by thin layer chromatography revealed the presence of starting material. The reaction mixture was cooled to [0 °C] and was treated with additional diisobutylaluminum hydride (6.0 mL, 6 mmol). After 4 h at rt, the reaction was quenched by the addition of water (10 mL) and the slurry was poured onto 5percent sodium hydroxide and dichloromethane (200 mL) and maintained for 30 min with vigorous stirring. The organic layer was separated, washed with brine, dried (sodium sulfate), and concentrated. The residue was dissolved in dichloromethane (100 mL) and was treated with manganese [(IV)] oxide (3.0 g) and powdered [4A] seives (3.0 g). The reaction mixture was filtered through Celite (100 mL dichloromethane rinse) after 14 h and the filtrate was extracted with 0.6 N aqueous sodium hydrogen sulite (2 x 150 mL). The combined aqueous layers were back-extracted with dichloromethane [(50] mL), were made basic (pH 11) by the addition of 50percent sodium hydroxide, and were extracted with ethyl acetate (2 x 100 mL). The ethyl acetate layers were dried (sodium sulfate) and concentrated to provide 268 mg (29percent) of the aldehyde as a tan solid. Data [: IHNMR (CDCL3) 6] 10.18 (s, 1H), 9.13 (s, [1H),] 8.61 (d, J= 1.0, 1H), 8.11 (d, J= 8.0, 1H), 8.01 (dd, J= 8.5, 1.5, 1H). Condensation: According to procedure A. Data: Yield: 86percent. 1H NMR (CD30D) 8 8.97 (s, 1H), 8.75 (s, [1H),] 8.60 (s, [1H),] 8.06 (d, [J=] 0.6, [1H),] 7. 87 (d, [J=] 8.4, [1H),] 7.82 (dt, Jd = 7.8, Jt = 1. 8, 1H), 7.30 (dd, J= 7.8, 4.8, 1H), 7.26 (dd, J= 8.4, 1.6, 1H), 6.76 (s, 1H), 3.86 (t, J= 5.5, 2H), 2.85 (m, 2H), 1.79 (m, 2H); MS [(EL)] m/z 306 [(M+ +] 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29% | Stage #1: With diisobutylaluminium hydride In dichloromethane at -35℃; for 0.25 h; Stage #2: With diisobutylaluminium hydride In dichloromethane at 0 - 20℃; for 4 h; |
Aldehyde preparation: To a solution of 4-chloro-3-nitrobeznoic acid (20 g, 99.2 mmol, 1.0 eq) in dimethylformamide (400 mL) was added potassium carbonate (35 g, 254 mmol, 2.55 eq). The mixture was stirred 30 min and ethyl iodide (18.6 g, 119 mmol, 1.20 eq) was added. The reaction mixture was stirred at 50 [°C] for 4h. Water (3 L) was added and the mixture was extracted with diethyl ether (2 x 500 mL). The organic extracts were combined, washed with brine (1 L), dried over anhydrous sodium sulfate and concentrated. The residue was crystallized from hexanes to provide 19.7 g (86percent) of the ester. Data [: IH] NMR (500 MHz, CDC13) [8] 8.51 (d, 1H), 8.17 (dd, 1H), 7.65 (d, 1H), 4.43 (q, 2H), 1.42 (t, 3H). Sulfur (1.60 g, 49.9 mmol, 0.58 eq) was dissolved in a solution of sodium sulfide [NONAHYDRATE] (12.0 g, 50.0 mmol, 0.58 eq) in water (60 [ML).] This solution was combined with a solution of ethyl 4-chloro-3-nitrobenzoate (19.6 g, 85.4 mmol, 1.00 eq) in ethanol (100 mL). The resulting mixture was heated at reflux for 3 h. The hot reaction mixture was poured into water (600 mL) and stirred for 15 min. The product was isolated by filtration and recrystallized from ethanol to provide 16.45 g (77percent) of the disulfide. Data: [APOS;H NMR] (500 MHz, CDC13) [5] 8.96 (d, 1H), 8.19 (dd, 1H), 7.88 (d, 1H), 4.43 (q, 2H), 1.41 (t, 3H). A mixture of diethyl 4,4'-dithiobis (3-nitrobenzoate) (11.2 g, 24.75 mmol, 1.00 eq) and zinc granules (15.0 g, 234 mmol, 9.47 eq) in formic acid (600 mL) was heated to reflux for 48 h. The mixture was cooled to room temperature and concentrated to dryness on vacuum rotary evaporator. The residue was partitioned between ethyl acetate (500 mL) and saturated aqueous sodium bicarbonate (500 mL). The organic layer was separated, dried over anhydrous sodium sulfate and concentrated on vacuum rotary evaporator. The residue was purified by chromatography on neutral Alumina (1/0 to 0/1 hexanes/dichloromethane) to provide 5.30 g (51percent) of the benzthiazole ester. Data: 1H NMR (500 MHz, [CDC13)] [8] [9. 08 (S, 1H),] 8.83 (d, 1H), 8.14 (dd, 1H), 8.02 (d, 1H), 4.45 (q, 2H), 1.44 (t, 3H); MS [(EI)] m/z 208 [(M++1).] Diisobutylaluminum hydride (1.0 M in dichloromethane, 6.0 mL, 6 mmol, 1.05 eq) was added over 15 min to a solution of the ester (1.18 g, 5.70 mmol) in dichloromethane (40 mL) [AT-35] [°C.] The reaction mixture was allowed to warm to rt and was maintained overnight. Analysis of the reaction progress by thin layer chromatography revealed the presence of starting material. The reaction mixture was cooled to [0 °C] and was treated with additional diisobutylaluminum hydride (6.0 mL, 6 mmol). After 4 h at rt, the reaction was quenched by the addition of water (10 mL) and the slurry was poured onto 5percent sodium hydroxide and dichloromethane (200 mL) and maintained for 30 min with vigorous stirring. The organic layer was separated, washed with brine, dried (sodium sulfate), and concentrated. The residue was dissolved in dichloromethane (100 mL) and was treated with manganese [(IV)] oxide (3.0 g) and powdered [4A] seives (3.0 g). The reaction mixture was filtered through Celite (100 mL dichloromethane rinse) after 14 h and the filtrate was extracted with 0.6 N aqueous sodium hydrogen sulite (2 x 150 mL). The combined aqueous layers were back-extracted with dichloromethane [(50] mL), were made basic (pH 11) by the addition of 50percent sodium hydroxide, and were extracted with ethyl acetate (2 x 100 mL). The ethyl acetate layers were dried (sodium sulfate) and concentrated to provide 268 mg (29percent) of the aldehyde as a tan solid. Data [: IHNMR (CDCL3) 6] 10.18 (s, 1H), 9.13 (s, [1H),] 8.61 (d, J= 1.0, 1H), 8.11 (d, J= 8.0, 1H), 8.01 (dd, J= 8.5, 1.5, 1H). Condensation: According to procedure A. Data: Yield: 86percent. 1H NMR (CD30D) 8 8.97 (s, 1H), 8.75 (s, [1H),] 8.60 (s, [1H),] 8.06 (d, [J=] 0.6, [1H),] 7. 87 (d, [J=] 8.4, [1H),] 7.82 (dt, Jd = 7.8, Jt = 1. 8, 1H), 7.30 (dd, J= 7.8, 4.8, 1H), 7.26 (dd, J= 8.4, 1.6, 1H), 6.76 (s, 1H), 3.86 (t, J= 5.5, 2H), 2.85 (m, 2H), 1.79 (m, 2H); MS [(EL)] m/z 306 [(M+ +] 1). |
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