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

HRID 1666732

Reaktionsgleichung

Reaktionsgleichung von HRID 1666732
[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]

Komponenten

6

Edukt 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)Benzenesulfonamide2×

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel

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

Quellen und Nachweise

ORD-Eintrag
ord-270cec2190294214aafeaed487ebda5f
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044089B2

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