Abstract
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.
Highlights
Quaternary ammonium salts have been used extensively in preparative organic chemistry
We were especially interested in benzamidomethylation of phenols, thiols, amines and dithiocarbamates in aqueous media using 1, because of the mild reaction conditions, high yields and simple isolation of products [3]
In the course of this work, we have carried out reactions of 1 with ammonia obtaining a mixture of di(benzamidomethyl)amine and tri(benzamido-methyl)amine [3]
Summary
Quaternary ammonium salts have been used extensively in preparative organic chemistry. We were especially interested in benzamidomethylation of phenols, thiols, amines and dithiocarbamates in aqueous media using 1, because of the mild reaction conditions, high yields and simple isolation of products [3]. In the course of this work, we have carried out reactions of 1 with ammonia obtaining a mixture of di(benzamidomethyl)amine and tri(benzamido-methyl)amine [3].
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