o-Chloranil → Diethyl 2-(thiazol-2(3H)-ylidene)malonate

HRID 881702

Reaktionsgleichung

Reaktionsgleichung von HRID 881702
C(OC([N:6]1[CH:10]=[CH:9][S:8][CH:7]1[CH:11]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=O)C.ClC1C(=O)C(=O)C(Cl)=C(Cl)C=1Cl>ClCCl>[S:8]1[CH:9]=[CH:10][NH:6][C:7]1=[C:11]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Komponenten

4

Edukt 2

HCID 73252o-ChloranilHCID 13331878HCID 13331878, Verbindung

Produkt 1

HCID 10977652Diethyl 2-(thiazol-2(3H)-ylidene)malonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of the product of Example 44A (12.9 g, 40.7 mmoles) in dichloromethane (100.0 ml) was added tetrachloro-1,2-benzoquinone (10.0 g, 40.7 mmoles) in portions at about 0° C., such that the mixture always had time to decolorize to a yellow-orange color. The mixture was then stirred for about 1 hour at 0° C. and was then washed with saturated aqueous sodium bicarbonate solution (200.0 ml) and brine (100.0 ml). The organic layer was dried over MgSO4, filtered, concentrated in vacuum and the crude product was purified by flash column chromatography on silica gel using hexanes/ethyl acetate (2:1) as the mobile phase to provide the title compound.

Aufarbeitung

  1. washwas then washed with saturated aqueous sodium bicarbonate solution (200.0 ml) and brine (100.0 ml)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuum
  5. customthe crude product was purified by flash column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-897d363fadf64e2dadeca438c9f29a34
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08993632B2

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