N-(2-aminophenyl)-4-chlorobenzenesulfonamide → 2-chloro-N-[2-(4-chloro-benzenesulfonylamino)phenyl]-5-trifluoromethylbenzenesulfonamide

HRID 730228Notes

Reaction equation

HRID 730228 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)(=[O:11])=[O:10].[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][C:21]=1[S:30](Cl)(=[O:32])=[O:31]>C(Cl)Cl.N1C=CC=CC=1>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:28])([F:27])[F:29])=[CH:22][C:21]=1[S:30]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][S:9]([C:12]1[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=1)(=[O:11])=[O:10])(=[O:32])=[O:31]

Participants

5

Reactant 2

HCID 241359N-(2-aminophenyl)-4-chlorobenzenesulfonamideHCID 27342742-Chloro-5-(trifluoromethyl)benzene-1-sulfonyl chloride

Product 1

HCID 689490302-chloro-N-[2-(4-chloro-benzenesulfonylamino)phenyl]-5-trifluoromethylbenzenesulfonamideYield 79.8%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-(2-amino-phenyl)-4-chlorobenzenesulfonamide (1.0 mmol, prepared as in Example 11) in DCM (2 mL) and pyridine (2 mL), 2-chloro-5-(trifluoromethyl)benzenesulfonyl chloride (1.1 mmol) was added at RT and the reaction mixture was then allowed to stir at RT overnight. The reaction mixture was then diluted with DCM (10 mL). The organic phase was washed with 10% aqueous HCl (10 mL), water (10 mL), and brine (10 mL). The organic phase was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue obtained was purified by flash column chromatography eluting with DCM/EtOAc to obtain 419 mg of 2-chloro-N-[2-(4-chloro-benzenesulfonylamino)phenyl]-5-trifluoromethylbenzenesulfonamide. LC: Tr 1.25 min; MS: 525.9 (M+1).

Workup

  1. washThe organic phase was washed with 10% aqueous HCl (10 mL), water (10 mL), and brine (10 mL)
  2. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe residue obtained
  5. customwas purified by flash column chromatography
  6. washeluting with DCM/EtOAc

Sources & evidence

ORD record
ord-7e7285c4c6c849808e8ba9c99bdcbcac
Source dataset
uspto-grants-2009_09
Patent number
US07582673B2

Reaction notes

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