Toluene → HCID 20563292, compound

HRID 1154778Notes

Reaction equation

HRID 1154778 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.C1(C)C=CC=CC=1.C(=O)([O-])O.[Na+].Cl[CH2:28][C:29]1[CH:36]=[CH:35][C:32]([CH:33]=[CH2:34])=[CH:31][CH:30]=1>O>[NH:7]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][CH2:28][C:29]2[CH:36]=[CH:35][C:32]([CH:33]=[CH2:34])=[CH:31][CH:30]=2)=[CH:10][CH:9]=1)[C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 7564N-Phenyl-p-phenylenediamineHCID 74126p-Vinylbenzyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 20563292HCID 20563292, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

36.8 g (0.2 mole) of p-aminodiphenylamine was added to 200 ml of toluene, and 16.8 g of sodium hydrogen carbonate and 30 ml of water was added. With stirring, 30.5 g (0.2 mole) of p-chloromethylstyrene was added dropwise to the mixture at 60° C. After the addition, the mixture was stirred at less than 60° C. for 4 hours. The resulting precipitate was separated, and washed with water to afford 49.8 g (yield 83%) of 4-anilino-N-(4-vinylbenzyl)aniline having a melting point of 143° C.

Workup

  1. additionwas added
  2. additionAfter the addition
  3. stirringthe mixture was stirred at less than 60° C. for 4 hours
  4. customThe resulting precipitate was separated
  5. washwashed with water

Sources & evidence

ORD record
ord-e9347d6004834421872c5998244d2296
Source dataset
uspto-grants-1981_11
Patent number
US04298522

Reaction notes

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