3-Thiazolidineacetic acid, 4-oxo-2-thioxo- → HCID 72394820, compound

Participants

Reaction Steps

A solution of rhodanine-3-acetic acid (87 mg, 0.46 mmol, 1 eq), 3-(1-phenyl-2,2,2-trifluoroethoxy)-4-(2-phenylethoxy)benzaldehyde (183 mg, 0.46 mmol, 1 eq) and sodium acetate (112 mg, 1.37 mmol, 3 eq) in acetic acid (2 mL) was heated to 150□C and stirred for 3.5 days. The reaction mixture was then cooled to room temperature and partitioned between ethyl acetate (50 mL) and water (50 mL) and the two layers separated. The organic layer was washed with 1M HCl (2×50 mL), and loaded onto silica. Elution with ethyl acetate:methanol (4:1) gave a yellow gum. This was dissolved in hot ethyl acetate and filtered (to remove some insoluble material). The filtrate was allowed to cool to room temperature and diethyl ether added. This gave a suspension which was again filtered. The filtrate was evaporated and the residue redissolved in diethyl ether. Addition of petroleum ether to the solution gave a precipitate which was filtered off. The mother liquor was evaporated and the resulting gum was crystallized from diethyl ether and petroleum ether to give the product as a yellow powder (107 mg, 41%) mp 170° C.: 1H NMR (d6 DMSO) δ 7.67 (s, 1H, C═C—H), 6.17 (q, 1H, J 6.5 Hz, CHCF3), 4.70 (s, 2H, CH2CO2H), 4.33 (t, 2H, J 5.9 Hz, OCH2CH2Ph), 3.09 (t, 2H, J 6.2 Hz, OCH2CH2Ph).

Provenance & Evidence