Reactions of (benzamidomethyl)triethylammonium chloride with some inorganic nucleophiles in aqueous media.
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.
Popovski
Emil
E
Institute of Chemistry, Faculty of Natural Sciences & Mathematics, Sts. Cyril and Methodius University, PO Box 162, 1000 Skopje, Macedonia. emilp@iunona.pmf.ukim.edu.mk
Bogdanov
Jane
J
Najdoski
Metodija
M
Hey-Hawkins
Evamarie
E
D001549:Benzamides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D013055:Spectrophotometry, Infrared; D014867:Water / Q000737:chemistry*
C526134:(benzamidomethyl)triethylammonium; D001549:Benzamides; D000644:Quaternary Ammonium Compounds; D014867:Water