Benzenesulfonyl chloride → N-(4-bromophenyl)-N-methylbenzenesulfonamide

HRID 2216546Notes

Reaction equation

HRID 2216546 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([NH:6][CH3:7])=[CH:4][CH:3]=1.[C:10]1([S:16](Cl)(=[O:18])=[O:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>N1C=CC=CC=1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([N:6]([CH3:7])[S:16]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)(=[O:18])=[O:17])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 2757052Benzenamine, 4-bromo-N-methyl-

Product 1

HCID 5171346N-(4-bromophenyl)-N-methylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 0.61 g (3.3 mmol) of 4-bromo-N-methylaniline and 0.5 mL (3.92 mmol) of benzenesulfonyl chloride in 5 mL of pyridine was stirred for 12 h at rt. After that time the pyridine was removed by azeotropic distillation with heptane. The residue was purified by chromatography on silica (hexanes:EtOAc, 9:1) to give the title compound.

Workup

  1. customAfter that time the pyridine was removed by azeotropic distillation with heptane
  2. customThe residue was purified by chromatography on silica (hexanes:EtOAc, 9:1)

Sources & evidence

ORD record
ord-90183b3ea6004d90b12f09ff8f255499
Source dataset
uspto-grants-2006_09
Patent number
US07112606B2

Reaction notes

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