Pyridine → 5-(4-Trifluoromethylphenylaminosulfonyl)-2-oxindole

HRID 24312

Reaction equation

HRID 24312 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].[F:15][C:16]([F:25])([F:24])[C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1.N1C=CC=CC=1>ClCCl>[F:15][C:16]([F:24])([F:25])[C:17]1[CH:18]=[CH:19][C:20]([NH:21][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:22][CH:23]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 99644-(Trifluoromethyl)anilineHCID 49625062-oxo-2,3-dihydro-1H-indole-5-sulfonyl chloride

Product 1

HCID 97987775-(4-Trifluoromethylphenylaminosulfonyl)-2-oxindoleYield 37.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 2.1 g of 5-chlorosulfonyl-2-oxindole, 1.6 g of 4-trifluoromethylaniline and 1.4 g of pyridine in 20 mL of dichloromethane was stirred at room temperature for 4 hours. The precipitate which formed was collected by vacuum filtration, washed twice with 5 mL of water and dried under vacuum at 40° C. overnight to give 2.4 g of crude product containing some impurities by thin layer chromatography. The crude product was chromatographed on silica gel eluting with ethyl acetate:hexane (1:2) to give 1.2 g (37% yield) of 5-(4-trifluoromethylphenyl-aminosulfonyl)-2-oxindole.

Workup

  1. customThe precipitate which formed
  2. filtrationwas collected by vacuum filtration
  3. washwashed twice with 5 mL of water
  4. customdried under vacuum at 40° C. overnight
  5. customto give 2.4 g of crude product
  6. additioncontaining some impurities by thin layer chromatography
  7. customThe crude product was chromatographed on silica gel eluting with ethyl acetate:hexane (1:2)

Sources & evidence

ORD record
ord-3dd397060f5746a9aec2d2ff10855546
Source dataset
uspto-grants-2005_02
Patent number
US06855730B2

Linked notes

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