Thiazolidinedione → 5-[4-(3-(5-Methyl-2-phenyl-4-oxazolyl)propionyl)phenylmethylene]thiazolidine-2,4-dione

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Reaction Steps

4-[3-(5-Methyl-2-phenyl-4-oxazolyl)propionyl]benzaldehyde, the title product of Preparation 4, (16 g, 0.05 mol), thiazolidine-2,4-dione (11.7 g, 0.10 mol and piperidine (0.85 g, 0.01 mol) were combined in 300 mL absolute ethanol, and the mixture refluxed for 24 hours, cooled to 0° C., diluted slowly with 600 mL of ether and, after stirring for 1 hour at 0° C., crude product recovered by filtration. The crude product was triturated with 150 mL of warm acetic acid (40°-50° C.). The resulting slurry was cooled to room temperature, diluted with 300 mL of ether, and 14.2 g (71%) of purified title product recovered by filtration; mp 224°-225° C.

Provenance & Evidence