Water → Isamoxole

Participants

Reaction Steps

2-(N-butylamino)-4-methyloxazole (106.7 g., 0.69 m.) and triethylamine (110 g., 0.77 m.) was stirred together in dry benzene (1500 c.c.) during the addition of isobutyrylchloride (81.0 g., 0.76 m.). The mixture was stirred at room temperature for 15 hours and then water (1 litre) was added. After stirring for a further hour the organic phase was separated, and the aqueous phase extracted twice in ether. The combined extract was washed successively with 2N hydrochloric acid (2 × 500 c.c.), 10% sodium carbonate solution (2 × 500 c.c.), and saturated brine (2 × 500 c.c.). Evaporation of the dried organic phase gave an oil, which was distilled to give 2-(N-butylisobutyramido)-4-methyloxazole, (118 g., 80%), b.p. 75-76° C./0.15 mm., which existed as an oil at room temperature but crystallised on cooling to 0° C.

Provenance & Evidence