Acetic Acid → 3-[(4-Nitrophenyl)sulfonyl]aminophenol

HRID 27654

Reaction equation

HRID 27654 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[N+:9]([C:12]1[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1)([O-:11])=[O:10].C(O)(=O)C>N1C=CC=CC=1>[N+:9]([C:12]1[CH:13]=[CH:14][C:15]([S:18]([NH:1][C:2]2[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=2)(=[O:20])=[O:19])=[CH:16][CH:17]=1)([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 74044-Nitrobenzenesulfonyl chlorideHCID 115683-Aminophenol

Product 1

HCID 223723493-[(4-Nitrophenyl)sulfonyl]aminophenolYield 56.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 3-aminophenol (33 g, 0.3 mole) and p-nitrobenzenesulfonyl chloride (66 g, 0.3 mole) in pyridine (350 ml) was heated at 80° on a steam bath for 4 hours. The reaction mixture was poured on ice and acidified with acetic acid. The precipitated product was filtered and recrystallized from isopropanol and gave 50 g (49%) of product which was used in Part B.

Workup

  1. temperaturewas heated at 80° on a steam bath for 4 hours
  2. additionThe reaction mixture was poured on ice
  3. filtrationThe precipitated product was filtered
  4. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-26a0e1480bfd42aead7188fc89038f4e
Source dataset
uspto-grants-1980_09
Patent number
US04222948

Linked notes

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