Imidazole → HCID 14514394, compound

Participants

Reaction Steps

3-Bromo-1-butyryloxybenzene is obtained by esterification of 3-bromophenol with butyric acid chloride and further is reacted, by Fries reaction and etherification of the phenolic hydroxyl group, with 2,4-dichlorobenzyl chloride into the 3-(2,4-dichlorobenzyloxy)-4-butyryl-1-bromobenzene. The 3(2,4-dichlorobenzyloxy)-4-butyrylbenzonitrile with a melting point of 97°-98° C. is obtained by reaction of substituted bromobenzene with copper(I) cyanide in N-methyl pyrrolidone (3 hours at 180° C.). The aromatic keto group is reduced with sodium boron hydride in aqueous dioxane to 3-(2,4-dichlorobenzyloxy)-4-(1-hydroxybutyl)-benzonitrile, melting point of 101°-105° C. The 3-(2,4-dichlorobenzyloxy)-4-(1-chlorobutyl)benzonitrile thionyl chloride. The substituted benzyl chloride is reacted with the sodium salt of the imidazole in dimethylformamide to 3-(2,4-dichlorobenzyloxy)-4-(imidazolyl)-butyl]-benzonitrile (melting point of 105°-107° C.).

Provenance & Evidence