Aniline → N-Phenyltetrachlorophthalimide

HRID 728324Notes

Reaction equation

HRID 728324 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>C(O)(=O)C>[Cl:13][C:5]1[C:4]([Cl:14])=[C:3]([Cl:15])[C:2]([Cl:1])=[C:7]2[C:8](=[O:10])[N:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:11](=[O:12])[C:6]=12

Participants

4

Reactant 2

HCID 6115AnilineHCID 8326Tetrachlorophthalic anhydride

Product 1

HCID 319375N-Phenyltetrachlorophthalimide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In a preferred embodiment tetrachlorophthalic anhydride is refluxed with aniline in the presence of glacial acetic acid for 5 to 10 hours to form tetrachloro-N-phenylphthalimide which is reacted with KF in sulfolane in the presence of tributylhexadecylophosphonium bromide under nitrogen at 140° C. to 160° C. for 10 to 15 hours to form tetrafluoro-N-phenylphthalimide which in turn is hydrolyzed by refluxing with 50% H2SO4 for 15 to 25 hours. The tetrafluoro-N-phenylphthalimide is a novel compound.

Sources & evidence

ORD record
ord-0c80dbaab8fa4a0d9a59256abf011562
Source dataset
uspto-grants-1991_09
Patent number
US05047553

Reaction notes

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