Synthesis and Characterization of Thiazolidinone Derivatives by Using Novel 1,3-dibutyl-1H- benzo[d]imidazol-3-ium Tetrafluroborate Ionic Liquid

Abstract

We have synthesized 1,3-dibutyl-1H-benzo[d]imidazol-3-ium tetrafluoroborate [DBBim] BF4 ionic liquid to carry out the synthesis of thiazolidin-2,4-one derivatives through substituted aldehydes, p-toluidine, and thioglycolic acid in a one-pot three-component synthesis. The tetrafluoroborate anion-based ionic liquid has demonstrated noticeably higher activity in shorter reaction time compared to Br̅ based IL and catalysts in the literature. Such TSIL i.e. task-specific ionic liquid [DBBim] BF4 serves as a catalyst and solvent during the synthesis of thiazolidinone derivatives, providing a moderate to good yield. The synthesis of thiazolidinone derivatives was achieved in only 18–30 minutes with [DBBim]BF4 IL catalyst which otherwise typically requires 6–8 hours when using the standard approach. This promising activity with reduced reaction time was not lost upon subsequent runs as observed with other catalysts reported in the literature. Even, the DBBim BF4 IL was conveniently extracted from the reaction medium and reused further. The synthesized compounds were characterized by spectral analysis such as IR, 1H-NMR, 13C-NMR, GC-MS, and HRMS.