p-Toluidine → N~1~-(3-Chlorophenyl)-N~2~-(4-methylphenyl)ethane-1,2-diamine

HRID 971848Notes

Reaction equation

HRID 971848 reaction equation
Br.Br[CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[CH:7]=1.[CH3:13][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[Cl:12][C:8]1[CH:7]=[C:6]([NH:5][CH2:4][CH2:3][NH:18][C:17]2[CH:19]=[CH:20][C:14]([CH3:13])=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 7813p-ToluidineHCID 10340Sodium CarbonateHCID 12606987N-(2-Bromoethyl)-3-chloroaniline--hydrogen bromide (1/1)

Product 1

HCID 21312028N~1~-(3-Chlorophenyl)-N~2~-(4-methylphenyl)ethane-1,2-diamineYield 76.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture consisting of 15.8 gm of N-(2-bromo-ethyl)-3-chloro-aniline hydrobromide, 10.7 gm of 4-methyl-aniline, 50 ml of toluene and 15 gm of anhydrous sodium carbonate was refluxed for eight hours, while stirring. Thereafter, the reaction mixture was filtered, the filter cake was washed with ethyl acetate, and the filtrate was evaporated in vacuo, leaving 10 gm of an oil which was used as the starting material in Example 11 without further purification. It was identified to be N-(3-chloro-phenyl)-N'-(4-methyl-phenyl)-ethylenediamine.

Workup

  1. temperaturewas refluxed for eight hours
  2. filtrationThereafter, the reaction mixture was filtered
  3. washthe filter cake was washed with ethyl acetate
  4. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-a514ab7a09994b5487c82e7cac01daef
Source dataset
uspto-grants-1979_07
Patent number
US04161528

Reaction notes

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