2-(4-Oxo-2-thioxo-thiazolidin-3-ylamino)-benzoic acid → 2-{5-[1-[5-(4-Morpholin-4-yl-phenyl)-furan-2-yl]-meth-(e)-ylidene]-4-oxo-2-thioxo-thiazolidin-3-ylamino}-benzoic acid

Participants

Reaction Steps

A mixture of 2-(4-oxo-2-thioxo-thiazolidin-3-ylamino)-benzoic acid (0.089 g, 0.33 mmol), 5-(4-morpholin-4-yl-phenyl)-furan-2-carbaldehyde (0.091 g, 0.35 mmol) and ethylenediamine diacetate (0.063 g, 0.035 mmol) in methanol (10 mL) was stirred at room temperature for 18 h. The reaction mixture was poured into stirred 0.6 N aq sodium hydrogensulfite (50 mL). The mixture was vigorously stirred for 30 mm. The solid product was filtered off and washed on funnel successively with 0.6 N aq sodium hydrogensulfite (1 mL), water (2×2 mL), ether (2×1 mL) and hexanes (2 mL). The material was dried in a vacuum oven at 65° C. for 17 h to afford 2-{5-[1-[5-(4-morpholin-4-yl-phenyl)-furan-2-yl]-meth-(E)-ylidene]-4-oxo-2-thioxo-thiazolidin-3-ylamino}-benzoic acid (147 mg, 87%) as a solid. 1H NMR (400 MHz, DMSO-d6): 3.26 (2H, m), 3.76 (2H, m), 6.53 (1H, d, J=8.4 Hz), 6.87 (1H, m), 7.14 (2H, m), 7.17 (1H, d, J=3.6 Hz), 7.31 (1H, m), 7.40 (1H, d, J=4.0 Hz), 7.71 (1H, s), 7.76 (2H, m), 7.91 (1H, m), 10.4 (1H, bs). LC/MS: APCI 506.1, HPLC 92%.

Provenance & Evidence