Formamide → 4,5-Dianilinophthalimide

HRID 1376752Notes

Reaction equation

HRID 1376752 reaction equation
[NH:1]([C:8]1[CH:9]=[C:10]2[C:15](=[O:16])[O:14][C:12](=O)[C:11]2=[CH:17][C:18]=1[NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.C([NH2:29])=O>>[NH:1]([C:8]1[CH:9]=[C:10]2[C:15](=[O:16])[NH:29][C:12](=[O:14])[C:11]2=[CH:17][C:18]=1[NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 713FormamideHCID 962WaterHCID 22076399HCID 22076399, compound

Product 1

HCID 16974,5-Dianilinophthalimide

Procedure

A suspension of 21.9 g (66.3 mmol) of 4,5-bis(anilino)phthalic anhydride in 60 ml of formamide under argon atmosphere is heated at 125°-130° for 5 hours. The reaction mixture is cooled to 70°, and 250 ml of water are slowly added. This mixture is cooled to 0° for 30 minutes, and the reddish crystals are filtered off, washed with water and dried. Recrystallization from DMF/water yields the title compound in the form of orange crystals, m.p. 205°-207° C., FAB-MS: 330 [M+ +H].

Workup

  1. temperatureis heated at 125°-130° for 5 hours
  2. temperatureThe reaction mixture is cooled to 70°
  3. temperatureThis mixture is cooled to 0° for 30 minutes
  4. filtrationthe reddish crystals are filtered off
  5. washwashed with water
  6. customdried
  7. customRecrystallization from DMF/water

Sources & evidence

ORD record
ord-e0603adaa6af448caed64e20063b86c9
Source dataset
uspto-grants-1997_09
Patent number
US05663336

Reaction notes

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