N-Phenyl-o-phenylenediamine → N-[(3,4,5-trimethoxyphenyl)carbonyl)-N'-phenyl-phenylenediamine

HRID 741728Notes

Reaction equation

HRID 741728 reaction equation
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH2:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([O:28][CH3:29])[C:25]=1[O:26][CH3:27])[C:20](Cl)=[O:21]>C(OCC)C>[CH3:29][O:28][C:24]1[CH:23]=[C:19]([C:20]([NH:14][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:21])[CH:18]=[C:17]([O:16][CH3:15])[C:25]=1[O:26][CH3:27]

Participants

4

Reactant 2

HCID 68297N-Phenyl-o-phenylenediamineHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-

Product 1

HCID 19353961N-[(3,4,5-trimethoxyphenyl)carbonyl)-N'-phenyl-phenylenediamine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of N-phenyl-o-phenylenediamine (1.84 g, 10 mmol) in diethyl ether (90 ml) was stirred at room temperature as 3,4,5-trimethoxybenzoyl chloride (2.31 g, 10 mmol) in diethyl ether (40 ml) was added dropwise. The reaction mixture was then stirred overnight at room temperature. The solvents were then removed in vacuo leaving N-[(3,4,5-trimethoxyphenyl)carbonyl]-N'-phenylphenylenediamine.

Workup

  1. additionwas added dropwise
  2. customThe solvents were then removed in vacuo

Sources & evidence

ORD record
ord-de2900d07c7543b1b8ab38dc0e15dccc
Source dataset
uspto-grants-1996_09
Patent number
US05552426

Reaction notes

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