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Molecules 2000, 5(7), 927-936; doi:10.3390/50700927
Article

Benzamidomethylation with (Benzamidomethyl)triethylammonium Chloride. 2. A Simple Method for Benzamidomethylation of Thiols, Amines and Carboxylic Acids

1,* , 2 and 3
1 Institute of Chemistry, Faculty of Natural Sciences & Mathematics, Sts. Cyril and Methodius University, PO Box 162, 1000 Skopje, Macedonia 2 Faculty of Pharmacy, Sts. Cyril and Methodius University, 1000 Skopje, Macedonia 3 Rudjer Boskovic Institute, Bijenicka 54, HR-10001, Zagreb, Croatia
* Author to whom correspondence should be addressed.
Received: 27 March 2000 / Revised: 22 June 2000 / Accepted: 29 June 2000 / Published: 7 July 2000
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Abstract

Thiols and amines were benzamidomethylated in water solution at room temperature with (benzamidomethyl)triethylammonium chloride (1) in the presence of a small quantity of triethylamine (pH>9). Benzamidomethyl thioethers (3a-d) and (benzamidomethyl) amines or di(benzamidomethyl)amines (5) were obtained in high yields (>90%) as well as S(CH2NHBz)2 in a reaction of 1 with Na2S. Benzamidomethyl esters RCOOCH2NHBz were obtained (60-75%) in reactions of carboxylic acids with 1 in chloroform or dioxane.
Keywords: Benzamidomethylation; thiols; carboxylic acids; amines Benzamidomethylation; thiols; carboxylic acids; amines
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Popovski, E.; Klisarova, L.; Vikic-Topic, D. Benzamidomethylation with (Benzamidomethyl)triethylammonium Chloride. 2. A Simple Method for Benzamidomethylation of Thiols, Amines and Carboxylic Acids. Molecules 2000, 5, 927-936.

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