Water → [Amino(ethoxy)methylidene]propanedinitrile

A mixture of 12.9 g of potassium tricyanomethanide from I B, 40 ml of water and 120 ml of diethyl ether was cooled to 5°. To this mixture was added 10 g of concentrated sulfuric acid dropwise at such a rate as to keep the reaction mixture temperature below 10°. Upon complete addition of sulfuric acid, the reaction mixture was stirred during 20 minutes. The mixture was then placed in a separatory funnel and the middle layer drawn off to be used in the next reaction. To 50 ml of the solution from above was added 150 ml of ethanol and volatile material was removed until the boiling temperature exceeded 50°, when the mixture was heated to reflux. The mixture was maintained at the reflux temperature for 15 hours. The white slurry was cooled to 10°, and the solid collected by filtration to give 6.5 g of 3-amino-3-ethoxy-2-cyano-2-propenenitrile, m.p. 233°. A small sample was recrystallized from ethanol without change of melting point. the nmr spectrum was consistent with the assigned structure.