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

HRID 2396049Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2396049
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

Komponenten

5

Edukt 3

HCID 222AmmoniaHCID 5234Sodium ChlorideHCID 10000342HCID 10000342, Verbindung

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 174Ethylene GlycolLösungsmittel

Versuchsvorschrift

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].

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-86a79904d4a64327947145a228f3808d
Quelldatensatz
uspto-grants-1996_02
Patentnummer
US05491144

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