Benzenesulfonyl chloride → N-(m-Nitrophenyl)benzenesulphonamide

HRID 2227575Notes

Reaction equation

HRID 2227575 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 (48.2 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 (Na2SO4) and concentrated to give 9.62 g (86%) of the title compound as a light tan solid. 1H-NMR (300 MHz, CDCl3) δ 7.96 (m, 2 H), 7.86 (m, 2 H), 7.41-7.63 (m, 5 1), and 7.30 (br s, 1 H). Mass spectrum (MALDI-TOF, gentisic acid matrix) calcd. for C12H10N2O4S: 301.0 (M+Na). Found: 301.1.

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 (Na2SO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-0e3d842b48d944a5942e6254930de3ab
Source dataset
uspto-grants-2002_07
Patent number
US06414020B2

Reaction notes

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