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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 16
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Original Articles

Solvent-Free Conversion of Thioamides to Thioesters

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Pages 2421-2429 | Received 12 May 2010, Published online: 14 Jun 2011
 

Abstract

Diverse thioesters were efficiently prepared via the solvent-free reaction of thioamide derivatives with alkyl halides in the presence of catalytic amounts of 1,4-diazabicyclo[2.2.2]octane (DABCO) in small quantities of water and in good to excellent yields.

ACKNOWLEDGMENT

The University of Isfahan, which provided facilities for this research, is gratefully acknowledged.

Notes

a Yields refer to isolated products.

b Formation of some colored impurities was observed.

a Thioamide derivative (1 mmol), alkyl halide (1 mmol), DABCO (0.05 mmol), temperature = 110 °C, time = 70 min.

b All products were characterized by IR, 1H NMR, 13C NMR, and elemental analysis.

c All yields refer to pure isolated products.

d Colorless to pale yellow liquids, which were crystallized very slowly (12–24 h), isolated by flash chromatography (silica gel, EtOAc–Hexane, 1:8).

e An excess amount of CH3I was added (2 mmol).

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