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Molecules 2006, 11(4), 279-285;

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
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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. View Full-Text
Keywords: Benzamidomethylation; inorganic nucleophiles; aqueous medium Benzamidomethylation; inorganic nucleophiles; aqueous medium

Figure 1

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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.

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