Thiazolidinedione → 5-{4-[2-(5-Methyl-2-phenyl-4-oxazolyl)ethoxy]benzylidene}-2,4-thiazolidinedione

Participants

Reaction Steps

A mixture of 4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzaldehyde (5.0 g), 2,4-thiazolidinedione (3.8 g), piperidine (0.32 ml) and ethanol (100 ml) was stirred under reflux for 5 hours. After cooling, the crystals which separated out were collected by filtration to give 5-{4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzylidene}-2,4-thiazolidinedione (5.1 g, 76.8%). Recrystallization from chloroform-ethanol afforded colorless needles, m.p. 213°-214° C. Elemental analysis for C22H18N2O4S, Calcd.: C, 65.01; H, 4.46; N, 6.89. Found: C, 64.81; H, 4.55; N, 6.78.

Provenance & Evidence