Hydrochloric Acid → 2-Hydroxy-5-[2-[4-[(2-pyridinylamino)sulfonyl]phenyl]ethenyl]benzoic acid

HRID 1464174노트

반응식

HRID 1464174 반응식
C([O:4][C:5]1[CH:17]=[CH:16][C:15]([CH:18]=[CH:19][C:20]2[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=2)=[CH:14][C:6]=1[C:7]([O:9]CC(C)C)=[O:8])(=O)C.[N:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[NH2:36].S(=O)(=O)(O)O.[OH-].[K+].Cl>ClCCl.C(O)C>[OH:4][C:5]1[CH:17]=[CH:16][C:15]([CH:18]=[CH:19][C:20]2[CH:25]=[CH:24][C:23]([S:26]([NH:36][C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][N:30]=3)(=[O:28])=[O:27])=[CH:22][CH:21]=2)=[CH:14][C:6]=1[C:7]([OH:9])=[O:8]

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 104392-AminopyridineHCID 14797Potassium HydroxideHCID 53789228Isobutyl 2-acetyloxy-5-[2-(4-(chlorosulfonyl)phenyl)ethenyl]benzoate

생성물 1

HCID 543430162-Hydroxy-5-[2-[4-[(2-pyridinylamino)sulfonyl]phenyl]ethenyl]benzoic acid

시약·촉매·용매 2

HCID 702Ethanol용매HCID 6344Dichloromethane용매2회

실험 절차

Isobutyl 2-acetyloxy-5-[2-(4-(chlorosulfonyl)phenyl)ethenyl]benzoate (1.99 g, 0.0046 mol) and 2-pyridinamine (1.3 g, 0.0138 mol) was stirred in dichloromethane (10 ml) at 45° C. for 1 h. After cooling to room temperature dichloromethane (20 ml) and 2M sulfuric acid (20 ml) were added. The precipitated solid (1.3 g) was collected and washed with water. The organic phase was taken to dryness and the residue treated with boiling methanol containing ammonia (2 ml) for 20 min. After cooling, 0.6 g was collected which was combined with the first crop. The combined material (1.9 g) was refluxed with potassium hydroxide (1 g) in water (50 ml). After acidification and filtration, the solid residue was dissolved in 70% ethanol with about 3 equivalents of potassium hydroxide at the boiling point and acidified while boiling with hydrochloric acid. After filtration and drying, the yield was 1.25 g (70%).

후처리

  1. additionwere added
  2. customThe precipitated solid (1.3 g) was collected
  3. washwashed with water
  4. additionthe residue treated with boiling methanol
  5. additioncontaining ammonia (2 ml) for 20 min
  6. temperatureAfter cooling
  7. custom0.6 g was collected which
  8. temperatureThe combined material (1.9 g) was refluxed with potassium hydroxide (1 g) in water (50 ml)
  9. filtrationAfter acidification and filtration
  10. filtrationAfter filtration
  11. customdrying

출처 및 근거

ORD 기록
ord-234b4b41977243faaa958ff2b5483e50
출처 데이터셋
uspto-grants-1994_04
특허 번호
US05302718

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