Pyridine → Benzenesulfonamide, N-(2,5-dimethylphenyl)-2-nitro-

HRID 1787443Notes

Reaction equation

HRID 1787443 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:3]=1[NH2:4].[N+:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[S:19](Cl)(=[O:21])=[O:20])([O-:12])=[O:11].N1C=CC=CC=1>C(Cl)Cl>[N+:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[S:19]([NH:4][C:3]1[CH:5]=[C:6]([CH3:9])[CH:7]=[CH:8][C:2]=1[CH3:1])(=[O:21])=[O:20])([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 1049PyridineHCID 72592,5-DimethylanilineHCID 155402-Nitrobenzenesulfonyl chloride

Product 1

HCID 779183Benzenesulfonamide, N-(2,5-dimethylphenyl)-2-nitro-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,5-dimethyl-aniline (2.4 g, 20 mmol) and 2-nitrobenzenesulfonyl chloride (4.4 g, 20 mmol) are dissolved in CH2Cl2 and treated with pyridine (1.8 mL, 22 mmol). The reaction mixture is stirred at room temperature until TLC shows no starting material. The reaction mixture is quenched with dilute HCl, and the organic layer washed with saturated brine. Drying over MgSO4, filtration, and concentration provides a solid that is recrystallized from hot EtOAc/hexanes to provide 2-nitro-N-(2,5-dimethyl-phenyl)-benzenesulfonamide.

Workup

  1. customThe reaction mixture is quenched with dilute HCl
  2. washthe organic layer washed with saturated brine
  3. dry with materialDrying over MgSO4, filtration, and concentration
  4. customprovides a solid
  5. customthat is recrystallized from hot EtOAc/hexanes

Sources & evidence

ORD record
ord-af36c5e5e898450ebf6f9c4a5cc84507
Source dataset
uspto-grants-2009_03
Patent number
US07511043B2

Reaction notes

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