THE REACTION OF CYANOGEN WITH ORGANIC COMPOUNDS VIII. 2-MERCAPTOETHYLAMINE AND ITS ALKYL DERIVATIVES¹

The Synthesis And Chemistry Of Cyanogen

“…More recently, it has been found that a similar reaction of mercaptoethylamine and cyanogen at 0°C. in an aqueous medium furnishes bis(A2-thiazolinyl) (XV) in 25.4 per cent yield (132, 221). No additional products were isolated.…”

“…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).…”

“…7. Alkoxyethylamines and 2-alkylmercaptoethylamines 2-Alkoxyethylamines (64,216) and 2-alkylmercaptoethylamines (132, 221) react with cyanogen in aqueous or alcoholic media to form the corresponding oxamidines (XVIII; XIX) (table 5). three methylene groups separate the two amino groups the aminoalkyloxamidines, which are first formed at low temperatures, decompose at room temperature to give fiveand six-membered ring compounds.…”

Trimerization of Benzonitrile with Sodium

“…The participation of both nitrogen atoms in alkylation of analogous cyclic amidines has been reported, for example, in the case of 4(5) methylimidazole, which yields 1,4-and 1,5-dimethylimidazoles on treatment with methyl iodide. 6 It seems therefore that the anion of I may be represented as a resonating system (V a,b,c) with…”

Imidates

“…(73) (11) Reaction of cyanogen with 2-mercaptoethylamine in aqueous solu tion [109]. (12) Reaction of cyanogen with methyl Cellosolve [10].…”