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

HRID 2197671

Reaction equation

HRID 2197671 reaction equation
[O:1]=[C:2]1[CH2:6][S:5][C:4](=[S:7])[N:3]1[CH:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]([OH:16])=[O:15])[CH2:9]1.[CH:17]1([C:23]2[CH:28]=[CH:27][C:26]([C:29]3[O:33][C:32]([CH:34]=O)=[CH:31][CH:30]=3)=[CH:25][CH:24]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.C(O)C>CO.ClCCl.[Cl-].[NH4+]>[CH:17]1([C:23]2[CH:28]=[CH:27][C:26]([C:29]3[O:33][C:32]([CH:34]=[C:6]4[S:5][C:4](=[S:7])[N:3]([CH:8]5[CH2:13][CH2:12][CH2:11][CH:10]([C:14]([OH:16])=[O:15])[CH2:9]5)[C:2]4=[O:1])=[CH:31][CH:30]=3)=[CH:25][CH:24]=2)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

7

Reactant 3

HCID 702EthanolHCID 594462253-(4-Oxo-2-thioxo-thiazolidin-3-yl)-cyclohexanecarboxylic acidHCID 594462355-(4-Cyclohexyl-phenyl)-furan-2-carbaldehyde

Product 1

HCID 866442943-{5-[1-[5-(4-Cyclohexyl-phenyl)-furan-2-yl]-methylidene]-4-oxo-2-thioxo-thiazolidin-3-yl}-cyclohexanecarboxylic acidYield 65.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 25517Ammonium ChlorideSolvent

Procedure

3-(4-oxo-2-thioxo-thiazolidin-3-yl)-cyclohexanecarboxylic acid (80 mg, 0.31 mmol), 5-(4-cyclohexyl-phenyl)-furan-2-carbaldehyde (84 mg, 0.33 mmol), and diethylenediamine diacetate (59 mg, 0.33 mmol) were combined in a 20 mL vial with ethanol (5 mL) and stirred at room temperature for 65 h. The reaction mixture was diluted with 10% methanol in dichloromethane (200 mL) and aqueous ammonium chloride (20 mL) and stirred at room temperature for 15 minutes. The layers were separated and the aqueous layer was extracted with 10% methanol in dichloromethane (2×100 mL). The combined organic extracts were washed with 0.6 N sodium hydrogensulfite (1×20 mL) and then brine (1×20 mL), dried (sodium sulfate) and concentrated under vacuum. The residue was triturated with dichloromethane/hexanes (1:5, 30 mL), filtered and dried overnight in a vacuum oven at 55° C. to afford 3-{5-[1-[5-(4-cyclohexyl-phenyl)-furan-2-yl]-methylidene]-4-oxo-2-thioxo-thiazolidin-3-yl}-cyclohexanecarboxylic acid (100 mg, 65%) as a solid. 1H NMR (400 MHz, DMSO-d6): δ 1.25-1.49 (7H, m), 1.67-1.92 (10H, m), 2.35-2.45 (2H, m), 2.56 (1H, m), 4.97 (1H, m), 7.26 (1H, d, J=3.6 Hz), 7.36 (1H, d, J=3.6 Hz), 7.42 (1H, d, J=8.4 Hz), 7.59 (1H, s), 7.77 (1H, d, J=8.4 Hz), 12.18 (1H, s); APCI-MS: 495.37; HPLC: 90%.

Workup

  1. stirringstirred at room temperature for 15 minutes
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with 10% methanol in dichloromethane (2×100 mL)
  4. washThe combined organic extracts were washed with 0.6 N sodium hydrogensulfite (1×20 mL)
  5. dry with materialbrine (1×20 mL), dried (sodium sulfate)
  6. concentrationconcentrated under vacuum
  7. customThe residue was triturated with dichloromethane/hexanes (1:5, 30 mL)
  8. filtrationfiltered
  9. customdried overnight in a vacuum oven at 55° C.

Sources & evidence

ORD record
ord-8c829be0a83a45b2988b25ad3f6fe6f0
Source dataset
uspto-grants-2012_12
Patent number
US08338465B2

Linked notes

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