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

HRID 491050

反応式

HRID 491050 の反応式
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]

参加物

4

反応物 2

HCID 73252o-ChloranilHCID 13331878HCID 13331878、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-960b55c652224fc8937b0e74251c1c80
出典データセット
uspto-grants-2009_05
特許番号
US07528282B2

関連ノート

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