3,4-Dimethylaniline → 4-chloro-N-(3,4-dimethyl-phenyl)-3-nitro-benzenesulfonamide

HRID 1514858Notes

Reaction equation

HRID 1514858 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[CH3:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][C:22]=1[CH3:23])[NH2:19].CN(C1C=CC=CN=1)C>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:19][C:18]2[CH:20]=[CH:21][C:22]([CH3:23])=[C:16]([CH3:15])[CH:17]=2)(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 72483,4-DimethylanilineHCID 7323Benzenesulfonyl chloride, 4-chloro-3-nitro-HCID 218852-Dimethylaminopyridine

Product 1

HCID 47954984-chloro-N-(3,4-dimethyl-phenyl)-3-nitro-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 4-chloro-3-nitro-benzenesulfonyl chloride (0.51 g) in pyridine (2 mL) were added 3,4-dimethylaniline and dimethylaminopyridine (0.024 g). The reaction mixture was stirred overnight, concentrated under reduced pressure, and diluted with CH2Cl2. The mixture was washed with water, dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography (SiO2, 1:3 EtOAc/Hexane) to give 4-chloro-N-(3,4-dimethyl-phenyl)-3-nitro-benzenesulfonamide.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additiondiluted with CH2Cl2
  3. washThe mixture was washed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (SiO2, 1:3 EtOAc/Hexane)

Sources & evidence

ORD record
ord-b907b49335894d668d476d85cdf71f58
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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