Ammonia → 4,5-Dianilinophthalimide

HRID 1376749Notes

Reaction equation

HRID 1376749 reaction equation
C[O:2][C:3](=O)[C:4]1[C:5](=[CH:10][C:11]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:12]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=1)[C:6](OC)=[O:7].[NH3:29]>C(O)CO>[NH:14]([C:12]1[CH:13]=[C:4]2[C:3](=[O:2])[NH:29][C:6](=[O:7])[C:5]2=[CH:10][C:11]=1[NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 10407176dimethyl 4,5-dianilinobenzene-1,2-dicarboxylate

Product 1

HCID 16974,5-Dianilinophthalimide

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

A suspension of 230 mg (0.7 mmol) of 4,5-bis(anilino)phthalic acid dimethyl ester in 23 ml of ethylene glycol is heated at 120°; ammonia gas is passed through the suspension, with stirring, for 24 hours. The reaction mixture is cooled and extracted with ethyl acetate. The ethyl acetate phases are washed in succession three times with water and once with saturated sodium chloride solution, dried with sodium sulfate and concentrated by evaporation. The evaporation residue is chromatographed on silica gel with dichloromethane/methanol 40:1 and the product fractions are combined and concentrated by evaporation, yielding the title compound in the form of yellow crystals, m.p. 215°-217°, FAB-MS: 330 [M+ +H].

Workup

  1. temperatureis heated at 120°
  2. temperatureThe reaction mixture is cooled
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate phases are washed in succession three times with water and once with saturated sodium chloride solution
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated by evaporation
  7. customThe evaporation residue is chromatographed on silica gel with dichloromethane/methanol 40:1
  8. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-be7c3ef965444e36ba33b12925829af8
Source dataset
uspto-grants-1997_09
Patent number
US05663336

Reaction notes

Loading…