Water → 1-(8-Cyanooctyl)-2,4,5-triphenyl-imidazole

Participants

Reaction Conditions

Reaction Steps

1-(8-Bromooctyl)-2,4,5-triphenylimidazole (4 g) in dimethylsulphoxide (30 ml) was added dropwise to a mixture of sodium cyanide (0.5 g) in dry dimethylsulphoxide (30 ml). The reaction mixture was stirred at 50° C. for 2 h, cooled and poured into water (400 ml). The aqueous was extracted with diethyl ether (4×100 ml), the extracts were combined, washed with water (100 ml), dried over anhydrous magnesium sulphate and evaporated to dryness in vacuo. Chromatography on silica gel eluted with a dichloromethane:methanol gradient and recrystallisation from ether gave 1-(8-cyanoctyl)-2,4,5-triphenylimidazole (1.1 g, 31%) as a white solid, m.p. 72°-73°. Found: C, 83.10; H, 7.21; N, 9.69%; C30H31N3 requires: C, 82.90; H, 7.19; N, 9.57%.

Provenance & Evidence