Water → HCID 19429354, compound

Participants

Reaction Steps

A solution of 2-methylimidazole (2.64 g) in dry tetrahydrofuran (THF) (40 ml ) was added over 1 minute to a stirred suspension of sodium hydride (1.54 g; 60% dispersion in oil) in THF (65 ml) under dry nitrogen. The mixture was stirred at ambient temperature for 1 hour, then heated to boiling under reflux and allowed to cool. A solution of 3-chloro-N-[1-(4-chlorophenyl)ethyl]-propionamide (5.7 g) in THF (25 ml) was added and the mixture stirred under reflux for 16 hours. The mixture was cooled and water (100 ml) was added portion-wise with stirring followed by ethyl acetate (200 ml). The acidic layer was separated and extracted with ethyl acetate and the combined ethyl acetate extracts extracted with hydrochloric acid (5M). The combined acidic extracts were basified with concentrated sodium hydroxide solution and extracted with ethyl acetate to give an oil. The oil was triturated with ether and filtered to give N-[1-(4-chlorophenyl)ethyl]-3-(2-methylimidazol-1-yl)propionamide, m.p. 135°-137° C.

Provenance & Evidence