5-Amino-2-methylphenol → 4-tert-butyl-N-(3-hydroxy-4-methylphenyl)benzenesulfonamide

HRID 16621

반응식

HRID 16621 반응식
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:20]=[C:19]([OH:21])[C:18]([CH3:22])=[CH:17][C:16]=2C2(C3C=CC=CC=3)C3C(=CC=CC=3)NC2=O)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(C1C=CC(S(Cl)(=O)=O)=CC=1)(C)(C)C.NC1C=CC(C)=C(O)C=1>ClCCl.N1C=CC=CC=1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:16]=[CH:17][C:18]([CH3:22])=[C:19]([OH:21])[CH:20]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 3

HCID 178185-Amino-2-methylphenolHCID 1398824-t-Butylbenzenesulfonyl chlorideHCID 104145404-Tert-Butyl-N-(5-Hydroxy-4-Methyl-2-(2-Oxo-3-Phenylindolin-3-Yl)Phenyl)Benzenesulfonamide2회

생성물 1

HCID 8380834-tert-butyl-N-(3-hydroxy-4-methylphenyl)benzenesulfonamide수율 78%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6344Dichloromethane용매

실험 절차

As another non-limiting example, 4-tert-butyl-N-[5-hydroxy-4-methyl-2-(2-oxo-3-phenyl-2,3 -dihydro-1H-indol-3-yl)-phenyl]-benzenesulfonamide (compound 1430) was synthesized by adding dropwise 4-tert-butyl-benzenesulfonyl chloride (8 g, 34 mmol) in 5 mL dichloromethane to a stirring solution of 5-Amino-2-methyl-phenol (4 g, 32 mmol) in 20 mL pyridine and letting the mixture spin overnight at room temperature. The resulting mixture was concentrated in vacuo and the product was purified by column chromatography to yield 8 g (78%) of 4-tert-butyl-N-(3-hydroxy-4-methyl-phenyl)-benzenesulfonamide. A mixture of 3-hydroxy-3-phenyl-1,3-dihydro-indol-2-one (3.9 g, 17 mmol), 4-tert-butyl-N-(3-hydroxy-4-methyl-phenyl)-benzenesulfonamide (7 g, 22 mmol) and p-toluenesulfonic acid (6.5 g, 32 mmol) in dichloroethane was refluxed for 12 hours. The resulting mixture was cooled to room temperature to yield a colorless solid. The solid was filtered and purified using column chromatography to yield 8 g (88%) of the desired product (compound 1430).

후처리

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. customthe product was purified by column chromatography

출처 및 근거

ORD 기록
ord-ff060df0401140c5a3fa3edda8adf338
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737172B2

연결된 노트

불러오는 중…