Reactions of (Benzamidomethyl)triethylammonium Chloride with Some Inorganic Nucleophiles in Aqueous Media

摘要

A variety of benzamidomethyl derivatives were prepared in water under alkaline conditions (pH>9) via reaction of (benzamidomethyl)triethylammonium chloride (>1) with different inorganic nucleophiles. Reaction of >1 with hydroxylamine did not give the expected mono(benzamidomethyl)-hydroxylamine (>3) but rather gave N,N-di(benzamidomethyl)hydroxylamine (>2). Reactions of >1 with sodium azide and potassium cyanide gave benzamidomethyl azide (>4a) and benzamidomethyl cyanide (>4b) respectively.  Potassium thiocyanate and sodium iodide reacted with >1, and the anion-exchanged products (benzamidomethyl)triethylammonium isothiocyanate (>5a) and (benzamidomethyl)triethylammonium iodide (>5b) were thus obtained. Cyanamide and potassium cyanate reacted readily with >1 and both gave the same mixture of di(benzamidomethyl)amine (>7) and tri(benzamidomethyl)amine (>8). All the reactions occurred smoothly, under mild conditions, to give the products in moderate to high yields.