Formamide → 5,6-Bis[(4-fluorophenyl)amino]-1H-isoindole-1,3(2H)-dione

HRID 2396043Notes

Reaction equation

HRID 2396043 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][C:5]([NH:6][C:7]2[CH:8]=[C:9]3[C:14](=[O:15])O[C:11](=[O:12])[C:10]3=[CH:16][C:17]=2[NH:18][C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)=[CH:4][CH:3]=1.O.C([NH2:31])=O>>[F:25][C:22]1[CH:23]=[CH:24][C:19]([NH:18][C:17]2[CH:16]=[C:10]3[C:11](=[O:12])[NH:31][C:14](=[O:15])[C:9]3=[CH:8][C:7]=2[NH:6][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:27][CH:26]=2)=[CH:20][CH:21]=1

Participants

4

Reactant 3

HCID 713FormamideHCID 962WaterHCID 22076403HCID 22076403, compound

Product 1

HCID 67111545,6-Bis[(4-fluorophenyl)amino]-1H-isoindole-1,3(2H)-dione

Procedure

A suspension of 1000 mg (2.73 mmol) of 4,5-bis(4-fluoroanilino)phthalic anhydride in 5 ml of formamide under argon atmosphere is heated at 125°-130° for 5 hours. The reaction mixture is cooled to 60°, and 20 ml of water are slowly added. This mixture is cooled to0° for 3 hours, and the reddish crystals are filtered off, washed with water and dried. Recrystallization from dichloromethane yields the title compound in the form of orange crystals, m.p. 244°-246° C., FAB-MS: 366 [M+ +H].

Workup

  1. temperatureis heated at 125°-130° for 5 hours
  2. temperatureThe reaction mixture is cooled to 60°
  3. temperatureThis mixture is cooled to0° for 3 hours
  4. filtrationthe reddish crystals are filtered off
  5. washwashed with water
  6. customdried
  7. customRecrystallization from dichloromethane

Sources & evidence

ORD record
ord-c6a27860002141efbb9c4406c6073d47
Source dataset
uspto-grants-1996_02
Patent number
US05491144

Reaction notes

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