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

HRID 2197676

반응식

HRID 2197676 반응식
[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.[F:17][C:18]([F:33])([F:32])[C:19]1[CH:20]=[C:21]([C:25]2[O:29][C:28]([CH:30]=O)=[CH:27][CH:26]=2)[CH:22]=[CH:23][CH:24]=1.C(O)C>CO.ClCCl.[Cl-].[NH4+]>[F:33][C:18]([F:17])([F:32])[C:19]1[CH:20]=[C:21]([C:25]2[O:29][C:28]([CH:30]=[C:6]3[S:5][C:4](=[S:7])[N:3]([CH:8]4[CH2:13][CH2:12][CH2:11][CH:10]([C:14]([OH:16])=[O:15])[CH2:9]4)[C:2]3=[O:1])=[CH:27][CH:26]=2)[CH:22]=[CH:23][CH:24]=1

참가 물질

7

반응물 3

HCID 702EthanolHCID 7218375-(3-(Trifluoromethyl)phenyl)furfuralHCID 594462253-(4-Oxo-2-thioxo-thiazolidin-3-yl)-cyclohexanecarboxylic acid

생성물 1

HCID 866442973-{5-[1-[5-(3-Trifluoromethyl-phenyl)-furan-2-yl]-methylidene]-4-oxo-2-thioxo-thiazolidin-3-yl}-cyclohexanecarboxylic acid수율 74%

시약·촉매·용매 3

HCID 887Methanol용매HCID 6344Dichloromethane용매HCID 25517Ammonium Chloride용매

실험 절차

3-(4-Oxo-2-thioxo-thiazolidin-3-yl)-cyclohexanecarboxylic acid (80 mg, 0.31 mmol), 5-(3-trifluoromethyl-phenyl)-furan-2-carbaldehyde (79 mg, 0.33 mmol) (purchased from Aldrich Chemical Company), 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-(3-trifluoromethyl-phenyl)-furan-2-yl]-methylidene]-4-oxo-2-thioxo-thiazolidin-3-yl}-cyclohexanecarboxylic acid (110 mg, 74%) as a solid. 1H NMR (400 MHz, DMSO-d6): δ 1.25-1.41 (2H, m), 1.67 (1H, m), 1.87-1.92 (3H, m), 2.29-2.45 (3H, m), 4.97 (1H, m), 7.37 (1H, d, J=3.6 Hz), 7.55 (1H, d, J=3.6 Hz), 7.62 (1H, s), 7.77-7.85 (2H, m), 8.11-8.18 (2H, m), 12.18 (1H, s); APCI-MS: 481.47; HPLC: 95%.

후처리

  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.

출처 및 근거

ORD 기록
ord-a2a6d7d9da784ffb9dbc843300a9f6e5
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08338465B2

연결된 노트

불러오는 중…