Aniline → N-Phenyltetrachlorophthalimide

HRID 622266Notes

Reaction equation

HRID 622266 reaction equation
[Cl:1][C:2]1[C:3]([Cl:15])=[C:4]([Cl:14])[C:5]([Cl:13])=[C:6]2[C:11](=[O:12])[O:10][C:8](=O)[C:7]=12.[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O1CCOCC1>[C:17]1([N:16]2[C:8](=[O:10])[C:7]3=[C:2]([Cl:1])[C:3]([Cl:15])=[C:4]([Cl:14])[C:5]([Cl:13])=[C:6]3[C:11]2=[O:12])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 8326Tetrachlorophthalic anhydride

Product 1

HCID 319375N-PhenyltetrachlorophthalimideYield 90%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In 1.2 l of dioxane was dissolved 286 g (1 mol) of tetrachlorophthalic anhydride, and while refluxing the solution, 93 g (1 mol) of aniline was added dropwise to the solution. Thereafter, the mixture was refluxed for 2 hours. The reaction mixture was allowed to cool, whereby tabular crystals were precipitated. The crystals were collected by filtration, washed with dioxane, and dried to provide 325 g of N-phenyltetrachlorophthalimide having a melting point of 251° C. to 253° C. (yield 90%).

Workup

  1. additionwas added dropwise to the solution
  2. temperatureThereafter, the mixture was refluxed for 2 hours
  3. temperatureto cool
  4. customwhereby tabular crystals were precipitated
  5. filtrationThe crystals were collected by filtration
  6. washwashed with dioxane
  7. customdried

Sources & evidence

ORD record
ord-655478e6c99745f4822bb9410ec1de09
Source dataset
uspto-grants-1988_09
Patent number
US04769493

Reaction notes

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