Triethylamine → Ethyl cyano{[(methanesulfonyl)oxy]imino}acetate

Participants

Reaction Steps

Ethyl 2-hydroxyimino-2-cyanoacetate (7.1 g) and triethylamine (7.0 ml) are dissolved in benzene (50 ml). To the solution is added dropwise a solution of methanesulfonyl chloride (3.9 ml) in benzene (8 ml) with stirring under ice-cooling and the mixture is stirred at the temperature for 3 hours and then allowed to stand overnight. The reaction mixture is filtered to remove the precipitates and the filtrate is concentrated to give crystals of ethyl 2-methanesulfonyloxyimino-2-cyanoacetate (10.6 g; 96.3%), melting point: 79°-83° C. The product is recrystallized from benzene-petroleum ether to give crystals having a melting point of 79°-81.5° C.

Provenance & Evidence