Acetic Acid → 2-Cyano-2-(methoxyimino)acetamide

Participants

Reaction Steps

To a stirred mixture of α-cyanoacetamide (252 g, 3 mole) and sodium nitrite (414 g, 6 mole) in water (600 ml) was added acetic acid (371 ml, 10 mole) at 5°-10° C. over 1.5 hours. The mixture was allowed to stir for another 1.5 hours and adjusted to pH 8.5 with 6N NaOH. To the mixture was added dimethyl sulfate (568 ml, 6 mole) at 15°-20° C. and the mixture was stirred at 45° C. for 1.5 hours. The reaction mixture was adjusted to pH 8.5 with 6N NaOH and allowed to stand at 5° C. overnight to separate the precipitate, which was collected by filtration, washed with cold water and air-dried to give 292 g (77%) of the title compound as brown needles melting at 170°-172° C.

Provenance & Evidence