4-Chloro-3-nitroaniline → N-(4-chloro-3-nitrophenyl)benzenesulfonamide

HRID 654586

Reaction equation

HRID 654586 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[S:12](Cl)([OH:15])(=O)=[O:13].[CH:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>N1C=CC=CC=1>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][S:12]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)(=[O:15])=[O:13])=[CH:3][C:4]=1[N+:9]([O-:11])=[O:10]

Participants

4

Reactant 2

HCID 124774-Chloro-3-nitroanilineHCID 22564087HCID 22564087, compound

Product 1

HCID 779563N-(4-chloro-3-nitrophenyl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
120 °C

Procedure

172.5 g (1 mol) of 4-amino-1-chloro-2-nitro-benzene are dissolved in 400 ml pyridine with heating. 193 g (1.09 mol) of benzene sulfochloride are slowly added dropwise, followed by heating for 1 hour at 120° C. (bath temperature). Subsequently, the solution is cast onto ice, and the 1-chloro-2-nitro-4-benzene-sulfonamido-benzene is evacuated in a vacuum. The compound is recrystallized from ethanol/water.

Workup

  1. temperaturewith heating
  2. customthe 1-chloro-2-nitro-4-benzene-sulfonamido-benzene is evacuated in a vacuum
  3. customThe compound is recrystallized from ethanol/water

Sources & evidence

ORD record
ord-95a47984e372496c92373e91e9a338ae
Source dataset
uspto-grants-1992_07
Patent number
US05132461

Linked notes

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