Acetonitrile → ethyl 1-methyl-1H-imidazole-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

N-methylnimdazole (320 g, 3.9 mol) was combined with 2 L acetonitrile and 1 L triethylamine in a 12 L flask equipped with a mechanical stirrer and the solution cooled to -20° C. Ethyl chloroformate (1000 g, 9.2 mol) was added with stirring, keeping the temperature between -20° C. and -25° C. The reaction was allowed to slowly warm to room temperature and stir for 36 h. Precipitated triethylamine hydrochloride was removed by filtration and the solution concentrated in vacuo at 65° C. The resulting oil was purified by distillation under reduced pressure (2 torr, 102° C.) to provide a white solid (360 g, 82% yield).

Provenance & Evidence