4-Toluenesulfonyl chloride → HCID 13956837, compound

HRID 2309410Notes

Reaction equation

HRID 2309410 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]1[CH:16]=[C:15]([CH3:17])[C:14]([O:18][CH3:19])=[C:13]([CH3:20])[CH:12]=1)=[C:5]2[CH3:21].[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1.C(OCC)(=O)C>N1C=CC=CC=1>[CH3:19][O:18][C:14]1[C:15]([CH3:17])=[CH:16][C:11]([C:6]2[NH:7][C:8]3[C:4]([C:5]=2[CH3:21])=[CH:3][C:2]([NH:1][S:28]([C:25]2[CH:26]=[CH:27][C:22]([CH3:32])=[CH:23][CH:24]=2)(=[O:30])=[O:29])=[CH:10][CH:9]=3)=[CH:12][C:13]=1[CH3:20]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 20185250HCID 20185250, compound

Product 1

HCID 13956837HCID 13956837, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1.85 g of 5-amino-2-(4-methoxy-3,5-dimethylphenyl)-3-methylindole was dissolved in 20 ml of pyridine, and 1.51 g of p-toluenesulfonyl chloride was added. The mixture was stirred at room temperature for 1 hour. Ethyl acetate was added to the reaction mixture, and the mixture was washed with 5% hydrochloric acid and water, and dried. The solvent was evaporated, and the residue was purified by silica gel column chromatography to give 2-(4-methoxy-3,5-dimethylphenyl)-3-methyl-5-p-toluenesulfonylaminoindole.

Workup

  1. washthe mixture was washed with 5% hydrochloric acid and water
  2. customdried
  3. customThe solvent was evaporated
  4. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9ac7fca7fa7d49828fa9076b06fd386e
Source dataset
uspto-grants-1987_09
Patent number
US04695581

Reaction notes

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