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

HRID 377237Notes

Reaction equation

HRID 377237 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'-phenyl-phenylenediamine.

Workup

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

Sources & evidence

ORD record
ord-bb6ee85fe22b44a5a32cd0927080d860
Source dataset
uspto-grants-2000_02
Patent number
US06025379

Reaction notes

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