title: Reactions of (benzamidomethyl)triethylammonium chloride with some inorganic nucleophiles in aqueous media.
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.
authors.affiliation: 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
authors.forename: Emil
authors.initials: E
authors.lastname: Popovski
authors.forename: Jane
authors.initials: J
authors.lastname: Bogdanov
authors.forename: Metodija
authors.initials: M
authors.lastname: Najdoski
authors.forename: Evamarie
authors.initials: E
authors.lastname: Hey-Hawkins
mesh_terms: D001549:Benzamides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D013055:Spectrophotometry, Infrared; D014867:Water / Q000737:chemistry*
chemical_list: C526134:(benzamidomethyl)triethylammonium; D001549:Benzamides; D000644:Quaternary Ammonium Compounds; D014867:Water