P-Phenylenediamine → N-(4-Aminophenyl)maleimide

HRID 2057047Notes

Reaction equation

HRID 2057047 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][C:4]([NH2:7])=[CH:3][CH:2]=1.[C:9]1(=O)[O:14][C:12](=[O:13])[CH:11]=[CH:10]1>O1CCCC1>[NH2:7][C:4]1[CH:5]=[CH:6][C:1]([N:8]2[C:12](=[O:13])[CH:11]=[CH:10][C:9]2=[O:14])=[CH:2][CH:3]=1

Participants

4

Reactant 2

HCID 7814P-PhenylenediamineHCID 7923Maleic Anhydride

Product 1

HCID 122469N-(4-Aminophenyl)maleimideYield 98.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

The solution of 21.6 g (200 mmol) of 1,4-phenylenediamine in 200 ml of tetrahydrofuran is mixed over 1.5 hours with the solution of 19.6 g of maleic acid anhydride, and it is stirred for 22 hours at 23° C. It is filtered, rewashed with tetrahydrofuran, and the filtrate is dried. 37.1 g (197 mmol, 98%) of the title compound is isolated as a crystalline solid.

Workup

  1. filtrationIt is filtered
  2. customthe filtrate is dried

Sources & evidence

ORD record
ord-929bcb8435194c3c8d4075d699a2972b
Source dataset
uspto-grants-2008_02
Patent number
US07335775B2

Reaction notes

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