4-Chlorobenzenesulfonyl chloride → HCID 68950965, compound

HRID 730234Notes

Reaction equation

HRID 730234 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[CH:7]=[CH:6][C:5]=1[NH2:16])([O-:3])=[O:2].[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>N1C=CC=CC=1.C(OCC)(=O)C>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([NH:16][C:5]2[CH:6]=[CH:7][C:8]([C:10]3[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=3)=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])(=[O:26])=[O:25])=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 10353230HCID 10353230, compound

Product 1

HCID 68950965HCID 68950965, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-nitro-4-pyridin-4-ylphenylamine (1 mmol) in pyridine (3 mL), 4-chloro-benzenesulfonyl chloride (1.2 mmol) was added and the resulting mixture was stirred at room temperature for 24 h. The reaction mixture was diluted with ethyl acetate (20 mL). The contents were washed with brine (25 mL), dried over sodium sulfate and concentrated under vacuum. The residue obtained was purified by column chromatography eluting with hexanes/ethyl acetate (1:1) then ethyl acetate to give 156 mg of 4-chloro-N-(2-nitro-4-pyridin-4-ylphenyl)benzene sulfonamide.

Workup

  1. washThe contents were washed with brine (25 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-4188ca5cb1eb47b0beb5f9c9f30521b5
Source dataset
uspto-grants-2009_09
Patent number
US07582673B2

Reaction notes

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