Hydrochloric Acid → HCID 9885141, compound

Participants

Reaction Steps

A mixture of methyl 3-{4-[2-acetoxy-2-(6-methyl-2-pyridyl)ethoxy]phenyl}-2-bromopropionate (3.2 g), thiourea (558 mg), sodium acetate (599 mg) and ethanol (30 ml) was heated under reflux for 4 hours, and then 6N-hydrochloric acid (30 ml) was added to the mixture, followed by heating under reflux for 16 hours. After neutralization with aqueous sodium hydrogencarbonate solution, the reaction mixture is extracted with chloroform, and the chloroform layer was washed with water and dried (MgSO4). After the solvent was distilled off, the residue was chromatographed on a silica-gel (100 g) column and elution was effected with benzene-acetone (10:1, V/V) to give 5-{4-[2-hydroxy-2-(6-methyl-2-pyridyl)ethoxy]benzyl}-2,4-thiazolidinedione in the form of crystals. Yield of 0.95 g. Recrystallization from ethyl acetate-hexane produced colorless prisms. m.p. 154°-155° C.

Provenance & Evidence