反应详情

23 mg of sodium hydride (as a 60% w/w dispersion in mineral oil) were added to a solution of 82 mg of methyl N-(4-hydroxy-2-methylphenyl)carbamate [prepared as described in Example 15(a) above] in 5 ml of dimethylformamide cooled in an ice-water bath. The resulting mixture was stirred at the same temperature for 15 minutes, and then 150 mg of 2-bromomethyl-6-methoxybenzothiazole [prepared as described in Example 6(a) above] were added. The temperature of the resulting mixture was elevated to room temperature and the mixture was stirred for 6 hours. At the end of this time, a saturated aqueous ammonium chloride solution 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 then removed by evaporation under reduced pressure and the resulting residue was purified by column chromatography through silica gel using a 2:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 110 mg (yield 68%) of the title compound as a solid having a melting point of 123° to 125° C.

1. temperaturecooled in an ice-water bath
2. customwas elevated to room temperature
3. stirringthe mixture was stirred for 6 hours
4. extractionthe resulting mixture was extracted with ethyl acetate
5. extractionThe resulting extract
6. washwas washed with water
7. dry with materialdried over anhydrous sodium sulfate
8. customThe solvent was then removed by evaporation under reduced pressure
9. customthe resulting residue was purified by column chromatography through silica gel using a 2:1
10. additionby volume mixture of hexane and ethyl acetate as the eluent