Acetic Acid → N-(4-hydroxyphenyl)-4-nitrobenzenesulfonamide

HRID 27655

Reaction equation

HRID 27655 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=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:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=2)(=[O:20])=[O:19])=[CH:16][CH:17]=1)([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4034-AminophenolHCID 74044-Nitrobenzenesulfonyl chloride

Product 1

HCID 352935N-(4-hydroxyphenyl)-4-nitrobenzenesulfonamideYield 73%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 4-aminophenol (27 g, 0.25 mole) and 4-nitrobenzenesulfonyl chloride (55 g, 0.25 mole) in pyridine (500 ml) was heated under reflux for 4 hours. The reaction mixture was poured in ice water and acidified with acetic acid. The crude product weighed 86 g. Recrystallization from CH3NO2 provided 53 g (73%) of material used in Part B; m.p. 197°-198°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. customRecrystallization from CH3NO2

Sources & evidence

ORD record
ord-74de4695fe0f4d1bb565c214767e9a0f
Source dataset
uspto-grants-1980_09
Patent number
US04222948

Linked notes

Loading…