Benzene → 4-(Phenylsulfonyl)aniline

HRID 735324Notes

Reaction equation

HRID 735324 reaction equation
[S:1]([OH:11])(=[O:10])([C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1)=O.[CH:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>FC(F)(F)C(O)=O>[C:12]1([S:1]([C:3]2[CH:4]=[CH:5][C:6]([NH2:9])=[CH:7][CH:8]=2)(=[O:10])=[O:11])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 241BenzeneHCID 8479Sulfanilic acidHCID 9845Trifluoroacetic anhydride

Product 1

HCID 5166664-(Phenylsulfonyl)aniline

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of sulfanilic acid (10 g, 0.52 mmol), benzene (4.7 g, 0.56 mmol) and trifluoroacetic anhydride (42 g) in trifluoroacetic acid (42 g) was heated to reflux for 3 days. The solvent was removed in vacuo and the residue taken up in 10% aqueous sodium hydroxide and heated to 100° C. for 15 minutes. The resulting white precipitate was filtered off, washed with water and dried to give [4-(phenylsulfonyl)phenyl]amine. 1H NMR (400 MHz, d6-DMSO) δ 7.83-7.81 (2H, m), 7.61-7.51 (5H, m), 6.62-6.58 (2H, m), 6.15 (2H, s).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 days
  3. customThe solvent was removed in vacuo
  4. filtrationThe resulting white precipitate was filtered off
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-283f2a691f9945d2a83777d64e8bb43a
Source dataset
uspto-grants-2009_09
Patent number
US07592456B2

Reaction notes

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