Acetic Acid → 5-{4-[2-(5-Methyl-2-phenyl-4-oxazolyl)-2-oxoethoxy]benzylidene}-2,4-thiazolidinedione

Participants

Reaction Steps

60% sodium hydride in oil (0.24 g) was added to a solution of 5-(4-hydroxybenzylidene)-2,4-thiazolidinedione (0.663 g) in N,N-dimethylformamide (20 ml) and the mixture was stirred for 30 minutes. Then, a solution of 4-bromoacetyl-5-methyl-2-phenyloxazole (0.841 g) in N,N-dimethylformamide (10 ml) was added dropwise to the mixture under ice-cooling. After stirring under ice-cooling for 30 minutes, the reaction solution was poured into ice-cold water. The aqueous mixture was made acid with acetic acid. The solid which precipitated was collected by filtration, washed with water, and crystallized from acetone to give 5-{4-[2-(5-methyl-2-phenyl-4-oxazolyl)-2-oxoethoxy]benzylidene}-2,4-thiazolidinedione (0.42 g, 32.3%). Recrystallization from chloroform-ethanol yielded colorless needles, m.p. 244°-245° C. Elemental analysis for C22H16N2O5S, Calcd.: C, 62.85; H, 3.84; N, 6.66. Found: C, 62.80; H, 3.69; N, 6.93.

Provenance & Evidence