Dimethyl Sulfoxide → Benzo[d][1,2,3]thiadiazole-7-carbaldehyde

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

Under nitrogen atmosphere, to a solution of oxalyl chloride (7.03 mL, 83.0 mmol) in methylene chloride (50 mL) was added dimethyl sulfoxide (8.84 mL, 125 mmol) and the mixture was stirred at −78° C. for 30 min. To the reaction mixture was added 1,2,3-benzothiadiazol-7-ylmethanol (6.90 g, 41.5 mmol) at −78° C. and the mixture was stirred for 2 hr. To the reaction mixture was added triethylamine (35.0 mL, 249 mmol) at −78° C. and the mixture was stirred for 30 min. The reaction mixture was warmed to room temperature, and stirred at room temperature for 4 hr. Saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with methylene chloride. 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 (methylene chloride/hexane) to give the title compound (6.20 g, yield 91%).

Herkunft & Nachweise