Potassium Carbonate → N,N'-diphenyl-N-(3-tolyl)-1,4-phenylenediamine

HRID 1168118Notes

Reaction equation

HRID 1168118 reaction equation
[C:1]1([N:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I[C:22]1[CH:23]=[C:24](C)[CH:25]=[CH:26][CH:27]=1.[C:29](=O)([O-])[O-].[K+].[K+]>[Cu].C1C2C(CCCC2)CCC1>[C:1]1([N:7]([C:15]2[CH:20]=[C:19]([CH3:29])[CH:18]=[CH:17][CH:16]=2)[C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 122683-IodotolueneHCID 75371N,N-Diphenyl-p-phenylenediamine

Product 1

HCID 21972152N,N'-diphenyl-N-(3-tolyl)-1,4-phenylenediamineYield 48.6%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7044DecalinSolvent

Procedure

In a 200 ml reaction vessel 26 grams of N,N-diphenyl-1,4-phenylenediamine and 22 grams of 3-iodotoluene were heated together with 0.3 grams of activated copper powders, 50 grams of potassium carbonate and 50 ml of decalin at an oil bath temperature of 200° C. for 24 hours in an Ar atmosphere. After the completion of the reaction, the reaction solution was filtrated with the addition of 100 ml of toluene thereto, thereby removing insolubles. The filtrate was washed with water, and dried over sodium sulfate. Following this, the solvent was removed by distillation from the filtrate, and the residue was purified twice by means of a silica gel column (using a mixed solvent of n-hexane and toluene as a developing solvent), thereby obtaining 17 grams of N,N′-diphenyl-N-(3-tolyl)-1,4-phenylenediamine.

Workup

  1. customAfter the completion of the reaction
  2. filtrationthe reaction solution was filtrated with the addition of 100 ml of toluene
  3. washThe filtrate was washed with water
  4. dry with materialdried over sodium sulfate
  5. customwas removed by distillation from the filtrate
  6. customthe residue was purified twice by means of a silica gel column (

Sources & evidence

ORD record
ord-45e47daea38f4b34a4dad5cecdb1351d
Source dataset
uspto-grants-2003_09
Patent number
US06623872B2

Reaction notes

Loading…