4-Chloroaniline → Bis(p-chlorophenyl)amine

HRID 359077Notes

Reaction equation

HRID 359077 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.[Cl:9][C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CS(C)=O>[CH:12]1[C:13]([NH:14][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[CH:15][CH:16]=[C:10]([Cl:9])[CH:11]=1

Participants

6

Reactant 4

HCID 78124-ChloroanilineHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 125101-Chloro-4-iodobenzene

Product 1

HCID 234111Bis(p-chlorophenyl)amineYield 35%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

p-Chloroiodobenzene (14 g), p-chloroaniline (11.23 g), potassium carbonate (12.15 g), and cuprous chloride (1.16 g) were suspended in dimethylsulfoxide (15 ml), and heated with stirring at 180°-190° C. for 3 hours and 40 minutes. After cooling the reaction mixture, ethyl acetate was added thereto, and washed with conc. aqueous ammonia 2 times, and with aqueous sodium chloride solution 3 times, and then, the mixture was concentrated under reduced pressure. The resulting residue was subjected to column chromatography on silica gel and eluted with a mixed solvent of chloroform/n-hexane [1:2 (v/v)] to give 4,4'-dichlorodiphenylamine (4.89 g).

Workup

  1. temperatureheated
  2. additionwas added
  3. washwashed with conc. aqueous ammonia 2 times
  4. concentrationwith aqueous sodium chloride solution 3 times, and then, the mixture was concentrated under reduced pressure
  5. washeluted with a mixed solvent of chloroform/n-hexane [1:2 (v/v)]

Sources & evidence

ORD record
ord-ab858852e9624f9f8654d570cdf433f7
Source dataset
uspto-grants-1991_03
Patent number
US04999378

Reaction notes

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