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

HRID 2387563Notes

Reaction equation

HRID 2387563 reaction equation
[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]

Participants

6

Reactant 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×

Product 1

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

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-425aac1f858f4b48b1145e9b3fa58661
Source dataset
uspto-grants-2012_09
Patent number
US08268879B2

Reaction notes

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