Potassium Carbonate → 2-Cyano-2-fluoromethoxyiminoacetamide

Participants

Reaction Steps

Potassium carbonate (85.7 g, 0.62 mol) was added to 2-cyano-2-hydroxyiminoacetamide (35.0 g, 0.31 mol) in dimethylsulfoxide (150 ml) under ice-cooling, and the mixture was stirred for 20 mins. On the other hand, a solution of fluoromethyl bromide (27.8 g, 0.31 mol) in dimethylformamide (27 ml) was added dropwise to the reaction mixture under ice-cooling, and the resultant mixture was stirred at a room temperature for 1.5 hrs. The mixture was dispersed in ice water (1 kg), and it was extracted three times with ethyl acetate (500 ml, 400 ml, and 300 ml, respectively). The combined extracts were washed twice with saturated brine (150 ml) and dried over magnesium sulfate (100 g). The ethyl acetate was distilled off under reduced pressure until the residue weighed 65.5 g. The residue was cooled, filtered, and dried to give 2-cyano-2-fluoromethoxyimino-acetamide (32.8 g, yield: 72.6%).

Provenance & Evidence