Dimethyl Sulfoxide → HCID 14835682, compound

Participants

Reaction Steps

Under nitrogen atmosphere, to a solution of oxalyl chloride (3.78 mL, 44.6 mmol) in dichloromethane (20 mL) was added dimethyl sulfoxide (4.75 mL, 66.9 mmol) at −78° C. and the mixture was stirred for 30 min. To the reaction mixture was added (2-methyl-1,3-benzothiazol-7-yl)methanol (4.00 g, 22.3 mmol) at −78° C. and the mixture was stirred for 2 hr. To the reaction mixture was added triethylamine (18.8 mL, 134 mmol) at −78° C. and the mixture was stirred for 30 min. The reaction mixture was warmed to room temperature, and the mixture was further stirred at room temperature for 4 hr. Saturated aqueous ammonium chloride solution was added and the mixture was extracted with dichloromethane. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by recrystallization (dichloromethane/hexane) to give the title compound (3.54 g, yield 90%).

Provenance & Evidence