Ammonia → HCID 22918357, compound

HRID 1376766Notes

Reaction equation

HRID 1376766 reaction equation
C[O:2][C:3](=O)[C:4]1[C:5](=[CH:10][C:11]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[I:29])=[C:12]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[I:21])[CH:13]=1)[C:6]([O:8]C)=O.[NH3:31]>C(O)CO.[Cl-].[Na+].O>[I:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[NH:22][C:11]1[CH:10]=[C:5]2[C:6](=[O:8])[NH:31][C:3](=[O:2])[C:4]2=[CH:13][C:12]=1[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[I:21]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 21753017HCID 21753017, compound

Product 1

HCID 22918357HCID 22918357, compound

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Analogously to Example 1, 1.48 g (2.36 mmol) of 4,5bis(2-iodoanilino)phthalic acid dimethyl ester in 25 ml of ethylene glycol are heated at 120° and, with stirring, ammonia gas is passed through the mixture for 19 hours. The reaction mixture is cooled, diluted with brine 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 residue obtained after concentration by evaporation is filtered through silica gel with dichloromethane and the product fractions are combined and concentrated by evaporation. The residue obtained after concentration by evaporation is crystallized from boiling dichloromethane, yielding the title compound in the form of yellow crystals, m.p. 108°-110° C., FAB-MS: 582 [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 residue obtained
  7. concentrationafter concentration
  8. customby evaporation
  9. filtrationis filtered through silica gel with dichloromethane
  10. concentrationconcentrated by evaporation
  11. customThe residue obtained
  12. concentrationafter concentration
  13. customby evaporation
  14. customis crystallized

Sources & evidence

ORD record
ord-c2f0b6a818f4490b9ce102fcbb5ef0b8
Source dataset
uspto-grants-1997_09
Patent number
US05663336

Reaction notes

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