Ammonia → 5,6-Bis(cyclohexylamino)-1H-isoindole-1,3(2H)-dione

HRID 2396049Notes

Reaction equation

HRID 2396049 reaction equation
C[O:2][C:3](=O)[C:4]1[C:5](=[CH:10][C:11]([NH:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[C:12]([NH:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:13]=1)[C:6](OC)=[O:7].[NH3:29].[Cl-].[Na+]>C(O)CO>[CH:15]1([NH:14][C:12]2[CH:13]=[C:4]3[C:3](=[O:2])[NH:29][C:6](=[O:7])[C:5]3=[CH:10][C:11]=2[NH:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 5234Sodium ChlorideHCID 10000342HCID 10000342, compound

Product 1

HCID 104500055,6-Bis(cyclohexylamino)-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

Analogously to Example 1, 194 mg (0.5 mmol) of 4,5-bis(cyclohexylamino)phthalic acid dimethyl ester in 15 ml of ethylene glycol are heated at 120°, ammonia gas being passed through the mixture, with stirring, for 12 hours. The reaction mixture is cooled, saturated with sodium chloride and extracted with ethyl acetate. The ethylacetate 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 hexane/ethyl acetate 3:1 and the product fractions are combined and concentrated by evaporation, yielding the title compound in the form of orange crystals, m.p. 170°-175° C., FAB-MS: 342 [M+ +H].

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethylacetate phases are washed in succession three times with water and once with saturated sodium chloride solution
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated by evaporation
  5. customThe evaporation residue is chromatographed onsilica gel with hexane/ethyl acetate 3:1
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-86a79904d4a64327947145a228f3808d
Source dataset
uspto-grants-1996_02
Patent number
US05491144

Reaction notes

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