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

HRID 881702

반응식

HRID 881702 반응식
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]

참가 물질

4

반응물 2

HCID 73252o-ChloranilHCID 13331878HCID 13331878, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-897d363fadf64e2dadeca438c9f29a34
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08993632B2

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