P-Phenylenediamine → HCID 19884453, compound

HRID 2249142Notes

Reaction equation

HRID 2249142 reaction equation
[CH:1]1[C:6]([NH2:7])=[CH:5][CH:4]=[C:3]([NH2:8])[CH:2]=1.[CH2:9](Br)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].[OH-].[Na+]>O>[CH2:9]([NH:7][C:6]1[CH:5]=[CH:4][C:3]([NH:8][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH3:9])=[CH:2][CH:1]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 7814P-PhenylenediamineHCID 82181-BromooctadecaneHCID 14798Sodium Hydroxide

Product 1

HCID 19884453HCID 19884453, compoundYield 40.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 15.6 g of p-phenylenediamine, 15.5 g of stearyl bromide, and 1.96 g of powdered sodium hydroxide was heated to 140° to 150° C. for about 3.5 hours with stirring under nitrogen gas stream. After the reaction was over, 50 ml of water was poured to the reaction mixture and black-purple solids thus formed were recovered by filtration. When the solids were washed with water, ethanol, and methylene chloride and filtered to provide about 5.8 g of a pink powder of N,N'-distearyl-p-phenylenediamine. The structure was confirmed by 1HNMR, IR spectra, and elemental analysis.

Workup

  1. temperaturewas heated to 140° to 150° C. for about 3.5 hours
  2. additionwas poured to the reaction mixture and black-purple solids
  3. customthus formed
  4. filtrationwere recovered by filtration
  5. washWhen the solids were washed with water, ethanol, and methylene chloride
  6. filtrationfiltered

Sources & evidence

ORD record
ord-536dcf63d698441a9029fc30befed775
Source dataset
uspto-grants-1991_08
Patent number
US05043248

Reaction notes

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