Dichloromethane → N-Methoxy-N,2-dimethylbenzo[d]oxazole-5-carboxamide

Participants

Reaction Steps

To a flask containing 2-methylbenzo[d]oxazole-5-carboxylic acid (1.00 g, 5.64 mmol) was added DCM (40 mL) to give a suspension. Carbonyldiimidazole (1.01 g, 6.21 mmol) was added and the mixture remained homogeneous and was stirred at room temperature for 17 hours, then N,O-dimethylhydroxylamine hydrochloride (688 mg, 7.06 mmol) was added and the mixture was stirred at room temperature for 18 hours. The contents were diluted with water and 1 N NaOH and extracted with DCM (4×50 mL). The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated. Flash chromatography on silica gel (10-40% EtOAc-DCM) gave the title compound as an amber oil.

Provenance & Evidence