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

HRID 1836610Notes

Reaction equation

HRID 1836610 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-11c9e94626cd4711b9d8b1bd3650d115
Source dataset
uspto-grants-2004_08
Patent number
US06777446B2

Reaction notes

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