Ammonia → HCID 22918420, compound

HRID 1376760Notes

Reaction equation

HRID 1376760 reaction equation
CO[C:3](=[O:44])[C:4]1[C:5](=[CH:10][C:11]([NH:29][C:30]2[CH:35]=[CH:34][C:33]([O:36][CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[CH:32][CH:31]=2)=[C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:17][CH:16]=2)[CH:13]=1)[C:6](OC)=[O:7].[NH3:45]>C(O)CO>[CH2:22]([O:21][C:18]1[CH:17]=[CH:16][C:15]([NH:14][C:12]2[CH:13]=[C:4]3[C:3](=[O:44])[NH:45][C:6](=[O:7])[C:5]3=[CH:10][C:11]=2[NH:29][C:30]2[CH:31]=[CH:32][C:33]([O:36][CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[CH:34][CH:35]=2)=[CH:20][CH:19]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 21753024HCID 21753024, compound

Product 1

HCID 22918420HCID 22918420, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

Analogously to Example 1, 294.4 mg (0.5 mmol) of 4,5-bis(4-benzyloxy-anilino)phthalic acid dimethyl ester in 22 ml of ethylene glycol are heated at 120°, ammonia gas being passed through the mixture, with stirring, for 16 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 50:1 and the product fractions are combined and concentrated by evaporation, yielding the title compound in the form of red crystals, m.p.187°-189° C., FAB-MS: 542 [M+ +H].

Workup

  1. temperatureThe reaction mixture is cooled
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate phases are washed in succession three times with water and once with saturated sodium chloride solution
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated by evaporation
  6. customThe evaporation residue is chromatographed on silica gel with dichloromethane/methanol 50:1
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-9ae9b9f84e4a464eb895c4c4d50c1bd6
Source dataset
uspto-grants-1997_09
Patent number
US05663336

Reaction notes

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