反应详情

0.13 ml of carbon disulfide were added to a stirred solution of 500 mg of 4-(benzothiazol-2-yl)methoxy-2-methylaniline [prepared as described in Example 21(b) below] and 114.5 mg of potassium hydroxide in 6 ml of dimethylformamide and 6 ml of water with cooling in an ice-water bath, and the resulting mixture was stirred for 10 minutes. The temperature of the mixture was then elevated to room temperature and the mixture was stirred for a further 30 minutes at this temperature. The reaction mixture was again cooled in an ice-water bath and 0.15 ml of methyl iodide were added thereto and the resulting mixture stirred at this temperature for 10 minutes. The temperature of the reaction mixture was then elevated to room temperature and the mixture was stirred at this temperature for 2.5 hours. At the end of this time, water was added to the reaction mixture and the resulting mixture was extracted with ethyl acetate. The resulting extract was washed with water and then dried over anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure to give a crude crystalline solid which was purified by column chromatography through silica gel using a 3:1 by volume mixture of hexane and ethyl acetate to give 458.2 mg (yield 68%) of the title compound as a solid having a melting point of 133°-135° C.

1. temperaturewith cooling in an ice-water bath
2. customwas then elevated to room temperature
3. stirringthe mixture was stirred for a further 30 minutes at this temperature
4. temperatureThe reaction mixture was again cooled in an ice-water bath
5. stirringthe resulting mixture stirred at this temperature for 10 minutes
6. customwas then elevated to room temperature
7. stirringthe mixture was stirred at this temperature for 2.5 hours
8. extractionthe resulting mixture was extracted with ethyl acetate
9. extractionThe resulting extract
10. washwas washed with water
11. dry with materialdried over anhydrous sodium sulfate
12. customThe solvent was removed by evaporation under reduced pressure
13. customto give a crude crystalline solid which
14. customwas purified by column chromatography through silica gel using a 3:1
15. additionby volume mixture of hexane and ethyl acetate