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Molecules 2006, 11(4), 279-285; doi:10.3390/11040279
Article

Reactions of (Benzamidomethyl)triethylammonium Chloride with Some Inorganic Nucleophiles in Aqueous Media

1,* , 1
, 1
 and 2
Received: 3 March 2006; Accepted: 9 April 2006 / Published: 10 April 2006
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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 Benzamidomethylation; inorganic nucleophiles; aqueous medium
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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.

AMA Style

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.

Chicago/Turabian Style

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.


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