Ethyl Acetate → HCID 86644298, Verbindung

HRID 2197677

Reaktionsgleichung

Reaktionsgleichung von HRID 2197677
[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.[Cl:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24]1[O:28][C:27]([CH:29]=O)=[CH:26][CH:25]=1.C(O)(=O)C.C(O)(=O)C.C(N)CN.C(OCC)(=O)C>C(O)C>[Cl:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24]1[O:28][C:27]([CH:29]=[C:6]2[S:5][C:4](=[S:7])[N:3]([CH:8]3[CH2:13][CH2:12][CH2:11][CH:10]([C:14]([OH:16])=[O:15])[CH2:9]3)[C:2]2=[O:1])=[CH:26][CH:25]=1

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 6098215-(2-Chlorophenyl)furfuralHCID 10154317Ethylenediamine diacetateHCID 59446225HCID 59446225, Verbindung

Produkt 1

HCID 86644298HCID 86644298, VerbindungAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

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%.

Aufarbeitung

  1. washwashed with 0.6 N aq sodium hydrogensulfite (2×50 mL)
  2. customThe organic layer was isolated
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude material was triturated with a mixture of ether (1 mL) and hexanes (3 mL)
  6. filtrationThe product was filtered off
  7. customdried in a vacuum oven at 60° C. for 17 h

Quellen und Nachweise

ORD-Eintrag
ord-91671b6cef594a5d9e53189f391383ed
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08338465B2

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