Imidazole → 4-(1-Imidazolylmethyl)benzonitrile

Participants

Reaction Steps

Under cooling, 23.15 g of imidazole in 250 ml of N,N-dimethylformamide is combined in portions with 14.8 g of sodium hydride, 60% in oil, and stirred for 1.5 hours at 25° up to the end of hydrogen release. In two portions, 50 g of 4-(bromomethyl)benzonitrile is added under ice cooling to this solution and the mixture is agitated for 1.5 hours at 25°. For processing, 100 ml of water is added under ice cooling, the mixture is agitated for 0.25 hour, poured into 1.5 1 of ethyl acetate, washed neutral with water, washed twice with sodium chloride and water, dried over sodium sulfate, concentrated to dryness under vacuum, and crystallized from acetone/diethyl ether, thus obtaining 33.6 g of 4-[1-(imidazolyl)methyl]benzonitrile as colorless crystals, mp 102°.

Provenance & Evidence