Pyridine → N-Methoxy-N,4-dimethyloxazole-5-carboxamide

Participants

Reaction Steps

4-Methyl-5-oxazolecarbonyl chloride (15g) and N,O-dimethylhydroxylamine hydrochloride (11 g) in dry chloroform (looml) were cooled to OOC and dry pyridine (28.5g) was added. The mixture was allowed to warm to room temperature. After 30 minutes aqueous sodium hydrogen carbonate was added and the organic layer separated. The aqueous layer was extracted with dichloromethane. The combined organic layers were washed, dried and evaporated. The residue was purified by flash chromatography to yield the title compound as a white solid. M.p. 59®-60° C. 1H Nmr (CDC3) 2.5, 3.34 and 3.82 (each 3H, s) and 7.86 (1H, S) ppm. Found: C, 49.0; H, 5.6; N, 16.4. C7H10N2O3 requires C, 49.4; H, 5.9; N, 16.5%

Provenance & Evidence