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

HRID 1944492노트

반응식

HRID 1944492 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 866522134-Benzenesulfonyl-3-chloroisothiazole-5-carbaldehyde수율 68%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-89b98cd6cbf543338570c08db5c8462e
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394836B2

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