THE REACTION OF CYANOGEN WITH ORGANIC COMPOUNDS. II. PRIMARY ALIPHATIC AMINES^{1, 2}

Abstract

In the first paper of this series (1) the production of cyanoformamidines from cyanogen and secondary amines was described.R2NH + (CN), -> R2NC(=NH)CNThe reaction was most satisfactory when anhydrous solvents such as ethyl acetate, benzene or toluene were employed, and no compounds were isolated in which both CN groups of cyanogen had undergone amine addition.It was interesting to discover, therefore, in extending the reaction to primary aliphatic amines, that in this case both CN groups reacted simultaneously with the production of symmetrically substituted oxamidines. NH NH 2 RNH2 + (CN), -» RNHC-CNHR

The Synthesis And Chemistry Of Cyanogen

“…Aromatic amines and ammonia were found by earlier workers to react readily with cyanogen to give oxamidines and numerous unidentified by-products, the identities of which have still not been determined. The reactions of aliphatic and heterocyclic amines with cyanogen, which had not been reported prior to 1950, have recently been studied in a comprehensive manner by Woodburn and associates (215,216,218,219,221,222).…”

The Reaction of Cyanogen with Organic Compounds. IV. Aminopyridines

“…Melting points are uncorrected. In the preparation and purification of cyanogen (3,4) the precaution should be taken to "condition" fresh charges of the alumina drying agent by first passing the gas through rather slowly until the entire tube is barely warm to the touch. Otherwise rapid preliminary absorption generates sufficient heat to cause tar formation in the tube.…”