Dimethyl Sulfoxide → HCID 86656159, compound

Participants

Reaction Steps

Dimethyl sulfoxide (1.13 mL, 0.016 mol) was added to oxalyl chloride (0.84 mL, 0.0099 mol) in methylene chloride (37.10 mL) at −78° C. After 10 minutes, (4-bromo-2-methyl-1,3-benzothiazol-5-yl)methanol (1.71 g, 0.00662 mol) in methylene chloride (74 mL) was added and the resultant mixture was stirred at −78° C. for 30 minutes. Triethylamine (4.62 mL, 0.0331 mol) was then added and the mixture was stirred for 5 h and the temperature allowed to gradually warm up to room temperature. After quenching with water, the mixture was extracted with methylene chloride. The organic layers were combined, washed with brine, dried over magnesium sulfate and evaporated to dryness. The resultant solid was used directly in next step (1.70 g, 100%). LCMS calculated for C9H7BrNOS(M+H)+: m/z=255.9; found: 255.9.

Provenance & Evidence