4-(Bromomethyl)benzonitrile → 3-[1-(4-Cyanobenzyl)-1H-imidazol-5-yl]-1-propanol

Participants

Reaction Steps

A solution of 97.0 g of 1-dimethylcarbamoyl-4-(3-trimethylsilyloxypropyl) -1H-imidazole and 72.0 g of 1-bromomethyl-4-cyanobenzene in 500 ml of acetonitrile is refluxed for 10 h. The solution is cooled to 0° in an ice bath and ammonia gas is bubbled in for a few minutes. The mixture is then evaporated in vacuo to give a semisolid which is dissolved in 500 ml of 1N hydrochloric acid. The solution is allowed to stand at room temperature for 15 min and then is extracted with ether. The pH of the aqueous phase is adjusted to 9 with 50% sodium hydroxide solution and the mixture is then extracted with methylene chloride. The methylene chloride extracts are washed with water, dried over sodium sulfate and evaporated to give a semi-solid which is triturated with cold acetone to yield the title compound (b) as a white solid, m.p. 121°-123°.

Provenance & Evidence