Benzenesulfonyl chloride → 2'-Chloro-4'-nitrobenzenesulfonanilide

HRID 399477Notes

Reaction equation

HRID 399477 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1[NH2:4].[C:12]1([S:18](Cl)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>N1C=CC=CC=1>[Cl:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1[NH:4][S:18]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:20])=[O:19]

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 84922-Chloro-4-nitroaniline

Product 1

HCID 2318362'-Chloro-4'-nitrobenzenesulfonanilide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-chloro-4-nitroaniline (4.33 g), benzenesulphonyl chloride (3.25 ml) and pyridine (2.5 ml) was stirred and heated to 100° C. for 18 hours. The mixture was cooled to ambient temperature and partitioned between methylene chloride and 2M aqueous hydrochloric acid. The organic phase was washed with water, dried and evaporated. The residue was recrystallised from ethyl acetate to give N-(2-chloro-4-nitrophenyl)benzenesulphonamide (6.07 g), m.p. 155°-157° C.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. custompartitioned between methylene chloride and 2M aqueous hydrochloric acid
  3. washThe organic phase was washed with water
  4. customdried
  5. customevaporated
  6. customThe residue was recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-c466971758344711aafc5413143c01f3
Source dataset
uspto-grants-1998_10
Patent number
US05821246

Reaction notes

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