Dimethylformamide → HCID 20265424, compound

Participants

Reaction Conditions

Reaction Steps

A solution of N-[3-(4-chlorobenzoyl)-5-methylisoxazol-4-yl]-bromoacetamide of Example Vc (4.26 g, 15.5 mmoles) in dimethylformamide (DMF) (40 ml) was added to a suspension of hexane-washed sodium hydride (0.67 g, 14 mmoles, 50% oil dispersion) in DMF (40 ml) at 5° C. After warming to 20° C., methyl iodide (1.06 ml, 17 mmoles) was added. The reaction solution was poured into dilute sodium bicarbonate (600 ml) with stirring. The precipitate was extracted with ethyl acetate, the organic solution was washed with water, saturated sodium chloride, and dried (sodium sulfate). Concentration gave a residue (5.5 g) which was chromatographed by high pressure liquid chromatography (HPLC) (8% ethyl acetate:dichloromethane) to give a solid that was pulverized to yield 3.0 g (66%) of a powder, melting point 133°-145° C.

Provenance & Evidence