Dimethylformamide → Isobutyl 2-acetyloxy-5-[2-(4-(chlorosulfonyl)phenyl)ethenyl]benzoate

HRID 1653911노트

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HRID 1653911 반응식
[K].[C:2]([O:5][C:6]1[CH:18]=[CH:17][C:16]([CH:19]=[CH:20][C:21]2[CH:26]=[CH:25][C:24]([S:27]([OH:30])(=O)=[O:28])=[CH:23][CH:22]=2)=[CH:15][C:7]=1[C:8]([O:10][CH2:11][CH:12]([CH3:14])[CH3:13])=[O:9])(=[O:4])[CH3:3].CN(C)C=O.S(Cl)([Cl:38])=O.[OH-].[Na+]>ClCCl.O>[C:2]([O:5][C:6]1[CH:18]=[CH:17][C:16]([CH:19]=[CH:20][C:21]2[CH:26]=[CH:25][C:24]([S:27]([Cl:38])(=[O:30])=[O:28])=[CH:23][CH:22]=2)=[CH:15][C:7]=1[C:8]([O:10][CH2:11][CH:12]([CH3:14])[CH3:13])=[O:9])(=[O:4])[CH3:3]

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 86747765Isobutyl 2-acetyloxy-5-[2(4-sulfophenyl)ethenyl]benzoate potassium salt

생성물 1

HCID 53789228Isobutyl 2-acetyloxy-5-[2-(4-(chlorosulfonyl)phenyl)ethenyl]benzoate

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

Isobutyl 2-acetyloxy-5-[2-(4-sulfophenyl)ethenyl]benzoate potassium salt (36.1 g, 0.08 mol) was suspended in dichloromethane. Dimethylformamide (20 ml) and thionyl chloride (20 ml) were added, and the mixture refluxed with stirring for 3 h. After cooling to room temperature, water (15 ml) was added. By careful addition of 5M sodium hydroxide, the pH of the aqueous phase was adjusted to about 7. The phases were separated and the organic phase washed with water. The solution was dried (MgSO4), treated with activated carbon and filtered. After evaporation of the solvent, the solid residue was recrystallized from a toluene and petroleum ether mixture. Yield 19.5 g (57%).

후처리

  1. temperaturethe mixture refluxed
  2. customThe phases were separated
  3. washthe organic phase washed with water
  4. dry with materialThe solution was dried (MgSO4)
  5. additiontreated with activated carbon
  6. filtrationfiltered
  7. customAfter evaporation of the solvent
  8. customthe solid residue was recrystallized from a toluene and petroleum ether mixture

출처 및 근거

ORD 기록
ord-c4ae5a9e02e24e8f8d5391af110b70d1
출처 데이터셋
uspto-grants-1995_04
특허 번호
US05403930

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