Hydrochloric Acid → 5-Phenylaminosulfonyl-2-oxindole

HRID 2101540Notes

Reaction equation

HRID 2101540 reaction equation
Cl[S:2]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8]2)(=[O:4])=[O:3].[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.N1C=CC=CC=1.Cl>ClCCl.C(OCC)(=O)C>[C:16]1([NH:15][S:2]([C:5]2[CH:6]=[C:7]3[C:11](=[CH:12][CH:13]=2)[NH:10][C:9](=[O:14])[CH2:8]3)(=[O:4])=[O:3])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6115AnilineHCID 49625062-oxo-2,3-dihydro-1H-indole-5-sulfonyl chloride

Product 1

HCID 163836185-Phenylaminosulfonyl-2-oxindole

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 5-chlorosulfonyl-2-oxindole (1.62 g, 7 mmol), aniline (0.782 mL, 8.4 mmol) and pyridine (1 mL) in dichloromethane (20 ml) was stirred at room temperature for 4 hours. The reaction mixture was diluted with ethyl acetate (300 mL) and acidified with 1N hydrochloric acid (16 mL). The organic layer was washed with sodium bicarbonate and brine, dried and concentrated. The residue was washed with ethanol (3 mL) and then chromatographed on silica gel eluting with methanol/dichloromethane 1:9 to give of 5-phenylaminosulfonyl-2-oxindole.

Workup

  1. washThe organic layer was washed with sodium bicarbonate and brine
  2. customdried
  3. concentrationconcentrated
  4. washThe residue was washed with ethanol (3 mL)
  5. customchromatographed on silica gel eluting with methanol/dichloromethane 1:9

Sources & evidence

ORD record
ord-4c2acd7e8dd74fda99427edf58870663
Source dataset
uspto-grants-2009_08
Patent number
US07572924B2

Reaction notes

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