Pyridine → 4-[4-(Benzenesulfonylamino)-phenyl]-butyric acid

HRID 1198192

반응식

HRID 1198192 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:4][CH:3]=1.[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.N1C=CC=CC=1>CC(C)=O>[C:14]1([S:20]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:6][CH:7]=2)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 270494-(4-Aminophenyl)butanoic acid

생성물 1

HCID 98400354-[4-(Benzenesulfonylamino)-phenyl]-butyric acid

시약·촉매·용매 1

HCID 180Acetone용매2회

실험 절차

To a solution of 4-(4-aminophenyl)butyric acid (1 g, 5.6 mmol) in dry acetone (30 ml) was added dropwise a solution of benzenesulphonyl chloride (0.99 g) and pyridine (1.1 g) in dry acetone (10 ml). The mixture was heated at reflux for 3 hours, then concentrated in vacuo. The resulting oil was dissolved in dichloromethane (100 ml) and the solution was washed with 2N aqueous HCl (2×100 ml), followed by water (2×100 ml). The dichloromethane solution was extracted with 10% aqueous NaOH (2×50 ml), followed by water (2×50 ml), and these extracts were combined and stirred with dichloromethane (100 ml) while conc. HCl was added to adjust the pH of the mixture to 5. The layers were separated and the organic solution was dried (MgSO04) and concentrated in vacuo. The resulting solid was recrystallised from isopropanol to give 4-[4-(phenyl-sulphonamido)phenyl]butyric acid. (1.03 g, 58%) mp. 128°-130 ° C.

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 hours
  3. concentrationconcentrated in vacuo
  4. dissolutionThe resulting oil was dissolved in dichloromethane (100 ml)
  5. washthe solution was washed with 2N aqueous HCl (2×100 ml)
  6. extractionThe dichloromethane solution was extracted with 10% aqueous NaOH (2×50 ml)
  7. additionwas added
  8. customThe layers were separated
  9. customthe organic solution was dried (MgSO04)
  10. concentrationconcentrated in vacuo
  11. customThe resulting solid was recrystallised from isopropanol

출처 및 근거

ORD 기록
ord-203b9b6dc5f64056803659a99d88da05
출처 데이터셋
uspto-grants-1994_01
특허 번호
US05280043

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