Aniline → N-Phenyltetrachlorophthalimide

HRID 728325Notes

Reaction equation

HRID 728325 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-PhenyltetrachlorophthalimideYield 96.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
114 °C

Procedure

Tetrachlorophthalic anhydride (300 g, 1.05 moles) was combined with aniline (100 g, 1.08 moles) and glacial acetic acid (3750 ml) in a 3-neck round bottom flask fitted with a cold-water condenser, overhead stirrer and a thermometer. The mixture was allowed to reflux (114° C.) with stirring for 6.5 hours. Crystallization occurred upon cooling. The crystals were filtered, washed with cold water and dried at 120° C., 0.5 mm Hg for 18 hours. 366 g tetrachloro-N-phenylphthalimide (96% yield) were recovered, mp 274°-275° C. The product was identified by gc/ms.

Workup

  1. customfitted with a cold-water condenser, overhead stirrer
  2. customCrystallization
  3. temperatureupon cooling
  4. filtrationThe crystals were filtered
  5. washwashed with cold water
  6. customdried at 120° C.
  7. wait0.5 mm Hg for 18 hours

Sources & evidence

ORD record
ord-de4381f608e947cfab309c0126b79226
Source dataset
uspto-grants-1991_09
Patent number
US05047553

Reaction notes

Loading…