N-(4-hydroxy-3-methylphenyl)acetamide

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 23.3 mg of sodium hydride (as a 60% w/w dispersion in mineral oil) were added to a solution of 97.7 mg of 4-acetamido-2-methylphenol in 3 ml of dimethylformamide cooled in an ice-water bath. The resulting mixture was stirred at the same temperature for 3 minutes, and then 132.2 mg of 2-bromomethylbenzothiazole [prepared as described in step (a) above] were added. The temperature of the resulting mixture was elevated to room temperature and the mixture was stirred for 3 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 consecutively with water and a saturated aqueous sodium chloride solution and then dried over anhydrous sodium sulfate. The solvent was then removed by evaporation under reduced pressure and the resulting residue was recrystallised from a mixed solvent of methylene chloride and hexane to give 85.7 mg (yield 82%) of the title compound as a solid having a melting point of 179° to 182° C. cooled in an ice-water bath was elevated to room temperature the mixture was stirred for 3 hours the resulting mixture was extracted with ethyl acetate The resulting extract was washed consecutively with water a saturated aqueous sodium chloride solution and then dried over anhydrous sodium sulfate The solvent was then removed by evaporation under reduced pressure the resulting residue was recrystallised from a mixed solvent of methylene chloride and hexane