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

HRID 2197676

反応式

HRID 2197676 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒HCID 25517Ammonium Chloride溶媒

実験手順

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%.

後処理

  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.

出典と根拠

ORDレコード
ord-a2a6d7d9da784ffb9dbc843300a9f6e5
出典データセット
uspto-grants-2012_12
特許番号
US08338465B2

関連ノート

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