Benzenesulfonyl chloride → N-(m-Nitrophenyl)benzenesulphonamide

HRID 651515Notes

Reaction equation

HRID 651515 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7])([O-:3])=[O:2].C(N(CC)C(C)C)(C)C.[C:20]1([S:26](Cl)(=[O:28])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(OCC)C>[N+:1]([C:4]1[CH:5]=[C:6]([NH:7][S:26]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=[O:28])=[O:27])[CH:8]=[CH:9][CH:10]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 74233-NitroanilineHCID 81531Diisopropylethylamine

Product 1

HCID 66459N-(m-Nitrophenyl)benzenesulphonamideYield 86%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 6.17 g (44.7 mmol) of 3-nitroaniline and 8.41 mL (482 mmol) of N,N-diisopropylethylamine in 150 mL of anhydrous diethyl ether was added 5.14 mL (40.2 mmol) of benzenesulfonyl chloride. The mixture was heated to reflux under nitrogen with stirring for 16 h, cooled and the resulting two-phase mixture scratched to crystallize the insoluble oil. After decanting the ether layer, the derived solid was dissolved in 300 mL of dichloromethane and the solution washed with 2 N HCl (3×200 mL), saturated NaHCO3 (200 mL), brine (200 mL), dried (NaO2SO4) and concentrated to give 9.62 g (86%) of the title compound as a light tan solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux under nitrogen
  3. temperaturecooled
  4. customto crystallize the insoluble oil
  5. customAfter decanting the ether layer
  6. dissolutionthe derived solid was dissolved in 300 mL of dichloromethane
  7. washthe solution washed with 2 N HCl (3×200 mL), saturated NaHCO3 (200 mL), brine (200 mL)
  8. dry with materialdried (NaO2SO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-2d4040aa56ae4e4488cabb4e1d6cba13
Source dataset
uspto-grants-2001_08
Patent number
US06281206B1

Reaction notes

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