4-Chlorobenzenesulfonyl chloride → 5-bromo-N-[2-(4-chlorobenzenesulfonylamino)-4-fluorophenyl]-2-methoxybenzenesulfonamide

HRID 730239Notes

Reaction equation

HRID 730239 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH3:21])=[C:6]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=2[NH2:19])(=[O:10])=[O:9])[CH:7]=1.[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1>N1C=CC=CC=1.C(Cl)Cl.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH3:21])=[C:6]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=2[NH:19][S:29]([C:26]2[CH:27]=[CH:28][C:23]([Cl:22])=[CH:24][CH:25]=2)(=[O:31])=[O:30])(=[O:10])=[O:9])[CH:7]=1

Participants

6

Reactant 2

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 689488865-bromo-N-(4-fluoro-2-aminophenyl)-2-methoxybenzenesulfonamide

Product 1

HCID 115992305-bromo-N-[2-(4-chlorobenzenesulfonylamino)-4-fluorophenyl]-2-methoxybenzenesulfonamideYield 78.2%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-bromo-N-(4-fluoro-2-aminophenyl)-2-methoxybenzenesulfonamide (0.1 mmol) in pyridine (0.5 mL) and DCM (2 mL), 4-chlorobenzenesulfonyl chloride (0.12 mmol) was added. The reaction mixture was stirred at room temperature for 4 h and then diluted with ethyl acetate (10 mL). The contents were washed with 10% aqueous HCl (10 mL) and brine (10 mL), dried over sodium sulfate, and concentrated under vacuum. The residue obtained was purified by column chromatography eluting with hexanes/ethyl acetate (1:1) followed by ethyl acetate to give 43 mg of 5-bromo-N-[2-(4-chlorobenzenesulfonylamino) -4-fluorophenyl]-2-methoxybenzenesulfonamide. LC: Tr 1.10 min, MS: 551.8 (M+1)+

Workup

  1. washThe contents were washed with 10% aqueous HCl (10 mL) and brine (10 mL)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe residue obtained
  5. customwas purified by column chromatography
  6. washeluting with hexanes/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-d8c9d71a0ef041cba4c306be9a74da85
Source dataset
uspto-grants-2009_09
Patent number
US07582673B2

Reaction notes

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