Dimethylformamide → 4-(Chloromethyl)-5-methyl-1-trityl-1H-imidazole

Participants

Reaction Steps

A solution of thionyl chloride (1.3 ml) in dry dichloromethane (10 ml) was added over 5 min to a stirred suspension of 5-methyl-1-(triphenylmethyl)-1H-imidazole-4-methanol (5.0 g) in a mixture of dichloromethane (100 ml) and dry DMF (2 ml) at 0°. The mixture was stirred at 0° for 0.5 h and washed consecutively with 8% sodium bicarbonate (2×50 ml), water (50 ml), dried and evaporated in vacuo below 40° to give an oil (5 g). This was dissolved in ether (100 ml) and the resulting solution filtered through a pad of silica which was further eluted with ether (2×100 ml). The combined filtrates were evaporated below 40° to give a white foam which was triturated with cold hexane and filtered to give the title compound (4.2 g) as a white crystalline solid, m.p. 133°-135°.

Provenance & Evidence