Aniline → Benzenesulfonamide, 3-nitro-N-phenyl-

HRID 1803917Notes

Reaction equation

HRID 1803917 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:10](Cl)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 6115AnilineHCID 84763-Nitrobenzenesulfonyl chlorideHCID 11430Potassium Carbonate

Product 1

HCID 120051Benzenesulfonamide, 3-nitro-N-phenyl-Yield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To 3-nitrobenzene-1-sulfonyl chloride (296.9 mg, 1.340 mmol) is added THF (20 mL), aniline (134.8 mg, 1.447 mmol) and potassium carbonate (408.5 mg, 2.955 mmol). The resulting mixture is heated at 50° C. for 16 hours. The reaction mixture is subsequently cooled and concentrated in vacuo after which the residue is treated with 10 ml of H2O and extracted with EtOAc (75 mL). The organic layer is washed with saturated aqueous NaCl (2×75 mL), dried (MgSO4), and concentrated in vacuo. The residue is purified over silica (CH2Cl2) to afford 257 mg (69% yield) of the desired compound. MS (ESI, pos. ion) m/z: 279 (M+1).

Workup

  1. temperatureThe reaction mixture is subsequently cooled
  2. concentrationconcentrated in vacuo after which the residue
  3. additionis treated with 10 ml of H2O
  4. extractionextracted with EtOAc (75 mL)
  5. washThe organic layer is washed with saturated aqueous NaCl (2×75 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified over silica (CH2Cl2)

Sources & evidence

ORD record
ord-e20a166f150a4546b06f168661161081
Source dataset
uspto-grants-2013_01
Patent number
US08354407B2

Reaction notes

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