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

doi:10.3390/50700927

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

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

Emil Popovski ¹^,* , Ljiljana Klisarova ² and Drazen Vikic-Topic 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; in revised form: 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

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MDPI and ACS Style

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.

AMA Style

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(7):927-936.

Chicago/Turabian Style

Popovski, Emil; Klisarova, Ljiljana; Vikic-Topic, Drazen. 2000. "Benzamidomethylation with (Benzamidomethyl)triethylammonium Chloride. 2. A Simple Method for Benzamidomethylation of Thiols, Amines and Carboxylic Acids." Molecules 5, no. 7: 927-936.

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