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

HRID 1057426Notes

Reaction equation

HRID 1057426 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 from example O-18, 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 was collected by vacuum filtration, washed twice with 5 mL of water each time 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-trifluoromethylphenylaminosulfonyl)-2-oxindole.

Workup

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

Sources & evidence

ORD record
ord-58eee44d4329460aa510911538b6abb0
Source dataset
uspto-grants-2003_02
Patent number
US06514981B1

Reaction notes

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