Ethyl Acetate → 3-{5-[1-[5-(2-Chloro-phenyl)-furan-2-yl]-methylidene]-4-oxo-2-thioxo-thiazolidin-3-yl}-cyclohexanecarboxylic acid

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A mixture of 3-(4-oxo-2-thioxo-thiazolidin-3-yl)-cyclohexanecarboxylic acid (0.038 g, 0.15 mmol), 5-(2-chloro-phenyl)-furan-2-carbaldehyde (0.033 g, 0.16 mmol) (purchased from Aldrich Chemical Company) and ethylenediamine diacetate (0.029 g, 0.16 mmol) in ethanol (5 mL) was heated to 60° C. for 4 h. The mixture was poured into ethyl acetate (250 mL) and washed with 0.6 N aq sodium hydrogensulfite (2×50 mL). The organic layer was isolated, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude material was triturated with a mixture of ether (1 mL) and hexanes (3 mL). The product was filtered off and dried in a vacuum oven at 60° C. for 17 h to afford 3-{5-[1-[5-(2-chloro-phenyl)-furan-2-yl]-methylidene]-4-oxo-2-thioxo-thiazolidin-3-yl}-cyclohexanecarboxylic acid as a solid (44 mg, 67%). H NMR (400 MHz, DMSO-d6): δ 1.25-1.31 (1H, m), 1.34-1.41 (1H, m), 1.69 (1H, m), 1.90 (3H, m), 2.28-2.45 (3H, m), 4.95 (1H, m), 7.40 (1H, d, J=3.6), 7.43 (1H, d, J=3.6), 7.46 (1H, m), 7.62 (1H, s), 7.62 (2H, m), 7.92 (1H, m), 12.22 (1H s). LC/MS: APCI 447.33, HPLC 100%.

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