Ammonia → 6-(Hydroxyimino)-5,5-dimethylthiomorpholin-3-one

Participants

Reaction Steps

A mixture of 12 g. of 1-ethoxycarbonylmethylthio-2-nitro-2-methylpropionaldoxime and 150 ml of ammonium hydroxide was charged into a pyrex pressure bottle and stirred at room temperature for three days. The excess ammonia and water was stripped from the reaction mixture under reduced pressure. The solid crystalline residue was washed with a small amount of cold water and dried. The residue was then recrystallized from acetonitrile to yield 4 g of 2-Oximino-3,3-dimethyltetrahydro-1,4-thiazin-5-one, m.p. 234°-236° C. The nmr and infrared spectra supported the proposed structure.

Provenance & Evidence