Comparative study of acid and basic catalysis in microwave assistance of Willgerodt-Kindler reaction for thiobenzamides and derivatives synthesis

Abstract

Montmorillonite K-10 was used in the acid catalysis of the Willgerodt-Kindler’s reaction (WK) under microwave heating for synthesis of thiobenzamides. Yields of 67% and 43% for the synthesis of morpholin- 4- yl (phenyl) methanethione (1) and [4 - (dimethylamino) phenyl] (morpholin-4-yl) methanethione (2) respectively, showed that the mixture (aldehyde, sulfur, morpholine and K-10) is quite suitable for this reaction. This enables to deduct that the conditions of acid catalysis with the K-10 are favourable to the WK’s reaction of carbonyl compounds. Furthermore, yields of 81% and 74% respectively for the synthesis of thioamides 1 and 2 in basic catalysis with 4-methylmorpholine allows to confirm that this reaction is more advantageous in basic catalysis. The structures of thioamides synthesized were characterized and confirmed by spectroscopy Infrared (IR), nuclear magnetic resonance (¹H and ¹³C NMR) and mass spectrometry (MS).

Keywords: Montmorillonite K-10, 4-methylmorpholine, morpholin-4-yl(phenyl)methanethione, [4- (dimethylamino)phenyl](morpholin-4-yl)methanethione