Oxalyl chloride → 5-methyl-1H-imidazole-4-carboxylic acid chloride

Participants

Reaction Steps

Under a dry nitrogen atmosphere, a stirred suspension of 5-methyl-1H-imidazole-4-carboxylic acid (12.6 g, 0.10 mole) and several drops of dimethylformamide in 125 ml of dry tetrahydrofuran was cooled in an ice bath. Oxalyl chloride, 20 ml, in 50 ml of tetrahydrofuran was carefully added dropwise. Upon complete addition the reaction mixture was heated under reflux for two hours, cooled to ambient temperature and diluted with 100 ml of diethyl ether. A solid precipitated and was collected by filtration, washed with diethyl ether, and dried to give 5-methyl-1H-imidazole-4-carboxylic acid chloride.

Provenance & Evidence