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Reactions of (Benzamidomethyl)triethylammonium Chloride with Some Inorganic Nucleophiles in Aqueous Media
Institute of Chemistry, Faculty of Natural Sciences & Mathematics, Sts. Cyril and Methodius University, PO Box 162, 1000 Skopje, Macedonia
Faculty of Chemistry and Mineralogy, University of Leipzig, Johannsallee 29, D-04103 Leipzig, Germany
* Author to whom correspondence should be addressed.
Received: 3 March 2006; Accepted: 9 April 2006 / Published: 10 April 2006
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.
Keywords: Benzamidomethylation; inorganic nucleophiles; aqueous medium
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Popovski, E.; Bogdanov, J.; Najdoski, M.; Hey-Hawkins, E. Reactions of (Benzamidomethyl)triethylammonium Chloride with Some Inorganic Nucleophiles in Aqueous Media. Molecules 2006, 11, 279-285.
Popovski E, Bogdanov J, Najdoski M, Hey-Hawkins E. Reactions of (Benzamidomethyl)triethylammonium Chloride with Some Inorganic Nucleophiles in Aqueous Media. Molecules. 2006; 11(4):279-285.
Popovski, Emil; Bogdanov, Jane; Najdoski, Metodija; Hey-Hawkins, Evamarie. 2006. "Reactions of (Benzamidomethyl)triethylammonium Chloride with Some Inorganic Nucleophiles in Aqueous Media." Molecules 11, no. 4: 279-285.