Ammonia → 2-Cyano-2-(methoxyimino)acetamide

Participants

Reaction Steps

To a solution of an aqueous concentrated ammonia (64.5 g, 1.07 mol) in water (28.7 ml), ethyl cyanoacetate (100 g, 0.89 mol) was added dropwise at -5° C. under ice-cooling. After completion of the reaction, the mixture was concentrated under reduced pressure. A solution of sodium nitrite (73.3 g, 1.06 mol) in water (151 g) was added to the residue. The mixture was maintained at an internal temperature of 38° to 48° C., to which 62.5% sulfuric acid (76.3 g, 0.49 mol) was added dropwise. After completion of the addition, the mixture was stirred at the same temperature for 1 hr, and then potassium carbonate (73.3 g, 0.53 mol) in water (110 g) was added dropwise followed by dimethyl sulfate (133.8 g, 1.06 mol) at 38° to 48° C. The mixture was stirred at the same temperature for 1 hr. and cooled. The resulting crystals were washed with water (150 ml) at 50° C., filtered and dried to give 2-cyano-2-methoxyimino-acetamide (92.2 g, yield: 82%).

Provenance & Evidence