Ethanol → 5-{4-[2-(5-Ethyl-2-pyridyl)ethoxy]benzyl}-2-imino-4-thiazolidinone

Participants

Reaction Steps

A mixture of the crude oil of methyl 2-bromo-3-{4-[2-(5-ethyl-2-pyridyl)ethoxy]phenyl}propionate (73.0 g) obtained in (b) thiourea (14.2 g), sodium acetate (15.3 g) and ethanol (500 ml) was stirred for 3 hours under reflux. The reaction mixture was concentrated under reduced pressure, and the concentrate wasneutralized with a saturated aqueous solution of sodium hydrogencarbonate, to which were added water (200 ml) and ether (100 ml). The whole mixture was stirred for 10 minutes to yield 5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzyl}-2-imino-4-thiazolidinone as crystals (0.3 g, 523.0%). Recrystallization from methanol gave colorless prisms, m.p. 187°-188° C. (decomp.). Elemental analysis for C19H21N3O2S Calcd.: C, 64.20; H, 5.95; N, 11.82. Found: C, 64.20; H, 5.84; N, 11.73.

Provenance & Evidence