Benzenesulfonyl chloride → Benzenesulfonamide, N-(4-nitrophenyl)-

HRID 1956456Notes

Reaction equation

HRID 1956456 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:11]1([S:17](Cl)(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>N1C=CC=CC=1>[C:11]1([S:17]([NH:8][C:7]2[CH:9]=[CH:10][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 74754-Nitroaniline

Product 1

HCID 231837Benzenesulfonamide, N-(4-nitrophenyl)-

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 4-nitroaniline (4-7) (13.8 g, 100 mmol) and phenylsulfonyl chloride (14 mL, 100 mmol) in pyridine (50 mL) was heated at 100° C. for 2 h. The resultant solution was concentrated, and the residue dissolved in ethyl acetate. The organic extract was washed successively with 2M hydrochloric acid, sat. aq. sodium bicarbonate brine, dried over magnesium sulfate, filtered and concentrated under vacuum. The residue was dissolved in a minimum amount of ethyl acetate with warning, and hexane added until the solution turned cloudy. The mixture was allowed to cool slowly to RT and then chilled at 0° C. The yellow solid precipitated was obtained by filtration. Further drying under vacuum overnight provide N-phenylsulfonyl-4-nitroaniline.

Workup

  1. concentrationThe resultant solution was concentrated
  2. dissolutionthe residue dissolved in ethyl acetate
  3. extractionThe organic extract
  4. washwas washed successively with 2M hydrochloric acid, sat. aq. sodium bicarbonate brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. dissolutionThe residue was dissolved in a minimum amount of ethyl acetate with warning, and hexane
  9. additionadded until the solution
  10. temperaturechilled at 0° C
  11. customThe yellow solid precipitated
  12. customwas obtained by filtration
  13. customFurther drying under vacuum overnight

Sources & evidence

ORD record
ord-515796fdc4424f8c8a84136218437d66
Source dataset
uspto-grants-1998_07
Patent number
US05780480

Reaction notes

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