Dimethyl Sulfoxide → 4-Benzenesulfonyl-3-chloroisothiazole-5-carbaldehyde

HRID 1944492ノート

反応式

HRID 1944492 の反応式
[Cl:1][C:2]1[C:6](Cl)=[C:5]([CH:8]=[O:9])[S:4][N:3]=1.[Na+].[C:11]1([S:17]([O-:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CS(C)=O>O>[C:11]1([S:17]([C:6]2[C:2]([Cl:1])=[N:3][S:4][C:5]=2[CH:8]=[O:9])(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

参加物

5

反応物 3

HCID 679Dimethyl SulfoxideHCID 2723840Benzenesulfinic acid, sodium saltHCID 866522123,4-Dichloro-1,2-thiazole-5-carbaldehyde

生成物 1

HCID 866522134-Benzenesulfonyl-3-chloroisothiazole-5-carbaldehyde収率 68%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of 3,4-dichloroisothiazole-5-carbaldehyde (0.087 g), benzenesulfinic acid sodium salt (0.078 g) and dimethyl sulfoxide (3.0 mL) was stirred at room temperature for 3.5 hours. The mixture was diluted with water and extracted with ethyl acetate. The combined organic extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel, eluting with a mixture of cyclohexane and ethyl acetate (1:0 to 0:1 by volume) to afford the title compound as a colourless oil (0.093 g).

後処理

  1. extractionextracted with ethyl acetate
  2. extractionThe combined organic extract
  3. washwas washed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel
  7. washeluting with a mixture of cyclohexane and ethyl acetate (1:0 to 0:1 by volume)

出典と根拠

ORDレコード
ord-89b98cd6cbf543338570c08db5c8462e
出典データセット
uspto-grants-2013_03
特許番号
US08394836B2

反応ノート

読み込み中…