Ethylenediamine diacetate → 3-{5-[1-[5-(4-Isobutyl-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 (0.075 g, 0.29 mmol), 5-(4-isobutyl-phenyl)-furan-2-carbaldehyde (0.069 g, 0.30 mmol) and ethylenediamine diacetate (0.057 g, 0.32 mmol) in anhydrous ethanol (12 mL) was stirred 30 h at ambient temperature. The reaction mixture was diluted with ethyl acetate (250 mL) and extracted with 0.6 N aq. sodium hydrogensulfite (2×50 mL). The organic layer was separated, dried over sodium sulfate and concentrated. The residue was triturated with hot acetonitrile (5 mL) and allowed to cool to room temperature. The product was filtered off, washed on the funnel with acetonitrile (0.5 mL) and dried in a vacuum oven at 60° C. for 17 h to afford 3-{5-[1-[5-(4-isobutyl-phenyl)-furan-2-yl]-methylidene]-4-oxo-2-thioxo-thiazolidin-3-yl}-cyclohexanecarboxylic acid (98 mg, 72%) as a solid. 1H NMR (400 MHz, DMSO-d6): δ 0.88 (6H, d, J=6.4 Hz), 1.16-1.45 (2H, m), 1.68 (1H, m), 1.84-1.92 (4H, m), 2.25-2.54 (3H, m), 4.98 (1H, m), 7.27 (1H, d, J=3.6 Hz), 7.36 (2H, m), 7.36 (1H, d, J=3.6 Hz), 7.58 (1H, s), 7.77 (2H, m), 12.22 (1H, s). LC/MS: APCI 469.51, HPLC 100%.

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