Ammonia → 4,5-Dianilinophthalimide

HRID 2396035Notes

Reaction equation

HRID 2396035 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 dimethylester 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 onsilica gel with dichloromethane/methanol 40:1 and the product fractions arecombined 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 onsilica gel with dichloromethane/methanol 40:1
  8. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-374d46e741ca4183a381aba4d3021e51
Source dataset
uspto-grants-1996_02
Patent number
US05491144

Reaction notes

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