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CAS No. : | 55690-60-3 | MDL No. : | MFCD00185941 |
Formula : | C8H7NOS2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | JDPITNFDYXOKRM-UHFFFAOYSA-N |
M.W : | 197.28 | Pubchem ID : | 2830679 |
Synonyms : |
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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 |
---|---|---|
With sulfuryl dichloride; at 0 - 20℃; for 2h; | Sulfuryl chloride (10 mL) was added to 5-methoxy-2- mercaptobenzothiazole at 0 0C. After complete addition, the reaction mixture was allowed to warm to it. After 2 h, the reaction mixture was poured into ice water (100 mL). This was allowed to warm to rt and was extracted with EtOAc (3 x). The combined organics were dried over Na2SO4, filtered, and concentrated under reduced pressure. The material was used without further purification. LC-MS: RT = 9.08 min., [M+H]+ = 234.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | With sulfuryl dichloride; In tetrahydrofuran; | Sulfuryl chloride (1.64 mL) was added to a solution of 5-methoxy-2- mercaptobenzothiazole in THF (20 mL). After stirring overnight, ice water was added. The reaction mixture was allowed to warm to rt and was diluted with EtOAc (100 mL). This was washed with water (50 mL) and brine (50 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure. The material was purified by column chromatography (0 to 3% EtOAc in hexanes gradient), yielding 0.407 g (20%) of the title compound as a white solid. LC-MS: RT = 9.05 min., [M+H]+ = 2O0.0. R/= 0.38 in 10% EtOAc/Hexanes. |
A mixture of 5-methoxy-1,3-benzothiazole-2-thiol (500 mg), thionyl chloride (2 mL) and DMF (1 drop) was stirred at 50 C. for 3 days. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the obtained mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (211 mg).1H NMR (300 MHz, DMSO-d6) δ 3.84 (3H, s), 7.15 (1H, dd, J=9.0, 2.5 Hz), 7.53 (1H, d, J=2.5 Hz), 7.97 (1H, d, J=9.0 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With potassium carbonate; In N,N-dimethyl-formamide; at 0 - 20℃; for 0.5h;Inert atmosphere; | To a mixture of 5-methoxy-1,3-benzothiazole-2-thiol (3.80 g, 19.2 mmol, CAS 55690-60-3) in DMF (50.0 mL) was added K2CO3 (5.32 g, 38.5 mmol) and CH3I (4.10 g, 28.8 mmol) at 0 C. The mixture was stirred at 20 C for 0.5 hour. On completion, the mixture was poured into the water (120 mL) and the aqueous phase was extracted with ethyl acetate (2 x 50 mL). The combined organic phase was washed with brine (2 X 50 mL), dried with anhydrous Na2SO4, filtered and concentrated in vacuo to give the title compound (4.00 g, 98% yield) as brown oil.1H NMR (400MHz, CDCl3) δ 7.60 (d, J = 8.8 Hz, 1H), 7.40 (d, J = 2.4 Hz, 1H), 6.94 (dd, J = 2.4, 8.8 Hz, 1H), 3.87 (s, 3H), 2.78 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bromine; In chloroform; at 0℃; for 1.5h; | Step 1.Synthesis of 2-bromo-5-methoxybenzothiazole A solution of bromine (3.6 eq) in chloroform (0.75M) was added dropwise over a period of 1 hr to a stirred suspension of <strong>[55690-60-3]5-methoxy-2-mercaptobenzothiazole</strong> (1 eq) in chloroform at 0 C. The mixture was stirred for 30 min before it was added slowly to water and stirred for further 20 min.The mixture was filtered to remove a cream solid.The organic phase was dried and evaporated to leave a brown solid.The brown solid was dissolved in ether and filtered.The residue was washed with ether and the filtrate and washings were combined and evaporated, chromatographed (4:1 hexanes and ethyl acetate) to give the title compound as a pale yellow solid. MS: MH+=244 | |
With bromine; In dichloromethane; chloroform; at 0 - 20℃; | A solution of bromine (1.2g, 7.5mmol) was added drop wise over a period of 1h to a stirred suspension of <strong>[55690-60-3]5-methoxy-2-mercaptobenzothiazole</strong> (1g, 5mmol) (7) in chloroform at 0oC. The mixture was stirred for 0.5h before it was added slowly to water and stirred for another 0.5h. The mixture was filtered to remove a creamy solid. The organic phase was dried with sodium sulfate and evaporated to obtain a brown solid. The brown solid was dissolved in ether and filtered. The residue was washed with ether and the filtrate and washings were combined and concentrated and chromatographed using 4:1 hexanes and ethyl acetate as the eluting solvent to give the title compound as a pale yellow solid. m/z: 242/244 (MH+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With methanol; potassium hydroxide;Heating / reflux; | 4-{4-(5-Methoxy-1,3-benzothiazol-2-thiolyl)butoxy}-7H-furo[3,2-g][1]benzopyran-7-on 539 mg (2.733 mmol) of 2-mercapto-5-methoxy-1,3-benzothiazole and 161 mg (2.869 mmol) of potassium hydroxide were refluxed in 25 ml of methanol until a clear solution was obtained. The solution was concentrated to dryness under vacuum. To the solid potassium salt was added 20 ml of anhydrous acetonitrile, 500 mg (1.708 mmol) of 5-(4-chlorobutoxy)psoralen, 333 mg (2.221 mmol) of sodium iodide and the resulting mixture was refluxed for 69 hours. The progress of the reaction was monitored by thin layer chromatography. After 69 hours the reaction mixture was concentrated under reduced pressure. The oily residue was cooled, diluted with water and acidified with concentrated hydrochloric acid to pH 1. The slurry was stirred for 15-20 min and extracted with 100 ml of dichloromethane. The dichloromethane layer was washed with 30 ml of 1% sodium hydroxide to separate the un-reacted 2-mercaptobenzothiazole followed by 30 ml of 2% hydrochloric acid, dried over anhydrous sodium sulfate and concentrated. The resulting oily residue was dissolved in methanol, treated with charcoal and re-crystallized from a petroleum ether-acetone (80:20) mixture. Yield: 599.8 mg (77.09%) Melting point: 134.8 C. 1H-NMR (500 MHz, CDCl3): δ [ppm]=8.09 (d, 1H, 3J=9.76 Hz, 3-H), 7.61 (d, 1H, 3J=8.9 Hz benzothiazole), 7.58 (d, 1H, 3J=2.24 Hz, 2'-H), 7.35 (d, 1H, 4J=2.2 Hz, benzothiazole), 7.14(s, 1H, 8-H), 6.97 (dd, 1H, 3J=8.9 Hz, 4J=2.1 Hz, benzothiazole), 6.95 (d, 1H, 3J=2.76 Hz, 3'-H), 6.18 (d, 1H, 3J=9.78 Hz, 4-H), 4.53 (t, 2H, 3J=5.78 Hz, 5-OC2CH2CH2CH2S-), 3.87 (s, 3H, O-C3), 3.48 (t, 2H, 3J=6.61 Hz, 5-OCH2CH2CH2C2S-), 2.11 (m, 4H, 5-OCH2C2C2CH2S-). MS (70 eV) m/z: 455 (6%, M+), 453 (44%), 328 (28%), 252 (100%, C12H14NOS2), 201 (6%), 196 (12%, C8H6NOS2), 174 (14%, [202-CO]+), 145 (8%), 89 (6%), 55 (28%, C4H7). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With triethanolamine; boron tribromide; In methanol; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; acetonitrile; | A. Preparation of 5-(2-chloroethoxy)-2-methylthio-benzothiazole To a 250 mL flask was added 2-mercapto-5-methoxybenzothiazole (5.1 g, 26 mmol), MeCN (63 mL), methyl p-toluenesulfonate (4.8 g, 26 mmol) and TEA (4.4 mL, 31 mmol). After stirring 16 h at ambient temperature, the solution was concentrated under reduced pressure. The crude material was diluted with EtOAc (200 mL), washed with water (2*75 mL), dried over Na2SO4, filtered, and concentrated. The resulting viscous oil was dissolved in DCM (40 mL), and transferred to an argon-purged 250 mL flask. The solution was cooled to -78 C. prior to the addition of a 1.0 M BBr3 solution in DCM (64 mL). The reaction suspension was allowed to warm to room temperature. After 16 h the reaction solution was cooled to -78 C. and quenched by addition of MeOH (100 mL). The resulting precipitates were isolated by vacuum filtration to yield 5-hydroxy-2-methylthio-benzothiazole (3.9 g, 76%) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 143 Preparation of N-{3-[3-benzyl-5-(5-methoxy-3-methyl-3H-benzothiazol-2-ylidene)-4-oxothiazolidin-2-ylideneamino]-4-ethylaminophenyl}-2-dimethylaminoacetamide The title compound was prepared in a manner similar to Example 1 by replacing 2-(methylthio)benzothiazole with 2-mercapto-5-methoxybenzothiazole and by replacing aniline with 3'-amino-2-dimethylamino-4'-ethylaminoacetanilide. MS(ESI): 603 (MH+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93.1% | 244 g of sodium polysulfide solution was mixed with 30 g of 1-chloro-4-methoxy-2-nitrobenzene, and then 20 mL of carbon disulfide was added with stiffing. The mixture was heated and refluxed for about 5 hrs and a yellow solid precipitated. The mixture was filtered and the filtrate was diluted with water to 1000 mL. An orange yellow solution was obtained. The solution was neutralized with hydrochloric acid (6M) to yield a light yellow solid. The solid was filtered, washed with water, and dried. 29.4 g of products was obtained with a yield of 93.1%. | |
(i) 2-Mercapto-5-methoxybenzthiazole yellow solid mp 198-200 C. (from 4-methoxy-2-nitrochlorobenzene) |
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