p-Toluenesulfonic acid → 4-Tert-Butyl-N-(5-Hydroxy-4-Methyl-2-(2-Oxo-3-Phenylindolin-3-Yl)Phenyl)Benzenesulfonamide

HRID 16622

Reaktionsgleichung

Reaktionsgleichung von HRID 16622
O[C:2]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:11].[C:18]([C:22]1[CH:27]=[CH:26][C:25]([S:28]([NH:31][C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[C:34]([OH:39])[CH:33]=2)(=[O:30])=[O:29])=[CH:24][CH:23]=1)([CH3:21])([CH3:20])[CH3:19].C1(C)C=CC(S(O)(=O)=O)=CC=1>ClC(Cl)C>[C:18]([C:22]1[CH:27]=[CH:26][C:25]([S:28]([NH:31][C:32]2[CH:33]=[C:34]([OH:39])[C:35]([CH3:38])=[CH:36][C:37]=2[C:2]2([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[NH:4][C:3]2=[O:11])(=[O:30])=[O:29])=[CH:24][CH:23]=1)([CH3:21])([CH3:20])[CH3:19]

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 158063-Hydroxy-3-phenyl-1,3-dihydroindol-2-oneHCID 8380834-tert-butyl-N-(3-hydroxy-4-methylphenyl)benzenesulfonamide

Produkt 1

HCID 104145404-Tert-Butyl-N-(5-Hydroxy-4-Methyl-2-(2-Oxo-3-Phenylindolin-3-Yl)Phenyl)BenzenesulfonamideAusbeute 89,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  1. temperaturewas refluxed for 12 hours
  2. customto yield a colorless solid
  3. filtrationThe solid was filtered
  4. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-54e5185f5a094c69b8faead1cbb2d43a
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737172B2

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