Aniline → 1H-Isoindole-1,3(2H)-dione, 4,5,7-trichloro-2-phenyl-

HRID 234781Notes

Reaction equation

HRID 234781 reaction equation
[Cl:1][C:2]1[C:10]([Cl:11])=[CH:9][C:8]([Cl:12])=[C:4]([C:5]([OH:7])=O)[C:3]=1[C:13]([OH:15])=O.[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(O)(=O)C>[Cl:1][C:2]1[C:10]([Cl:11])=[CH:9][C:8]([Cl:12])=[C:4]2[C:5]([N:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:13](=[O:15])[C:3]=12)=[O:7]

Participants

4

Reactant 2

HCID 6115AnilineHCID 111191343,4,6-trichlorophthalic Acid

Product 1

HCID 98838351H-Isoindole-1,3(2H)-dione, 4,5,7-trichloro-2-phenyl-Yield 97.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3,4,6-Trichlorophthalic acid (500 g, 1.86 moles), glacial acetic acid (4 L), and aniline (175 mL, 1.92 moles) were charged to a 12 L 3-neck flask equipped with a condenser, a stirrer and a thermometer. The mixture was heated with stirring and maintained at 100°-101° C. for 2 hours, then cooled to room temperature and filtered. The filter cake was washed with cold water and vacuum dried (70° C., 0.2 mmHg) for 24 hours to yield 590.7 g of 97.5% pure 3,4,6-trichloro-N-phenylphthalimide (m.p. 199°-200° C.).

Workup

  1. customequipped with a condenser, a stirrer
  2. temperatureThe mixture was heated
  3. temperaturemaintained at 100°-101° C. for 2 hours
  4. filtrationfiltered
  5. washThe filter cake was washed with cold water and vacuum
  6. customdried (70° C., 0.2 mmHg) for 24 hours

Sources & evidence

ORD record
ord-b05a60984205459288d4c4317d57952a
Source dataset
uspto-grants-1997_01
Patent number
US05596104

Reaction notes

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