Ammonia → Cgp53353

HRID 1376755Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1376755
C[O:2][C:3](=O)[C:4]1[C:5](=[CH:10][C:11]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)=[C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH:13]=1)[C:6](OC)=[O:7].[NH3:31]>C(O)CO>[F:21][C:18]1[CH:19]=[CH:20][C:15]([NH:14][C:12]2[CH:13]=[C:4]3[C:3](=[O:2])[NH:31][C:6](=[O:7])[C:5]3=[CH:10][C:11]=2[NH:22][C:23]2[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=2)=[CH:16][CH:17]=1

Komponenten

4

Edukt 2

HCID 222AmmoniaHCID 10476762HCID 10476762, Verbindung

Produkt 1

HCID 6711154Cgp53353

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 174Ethylene GlycolLösungsmittel

Versuchsvorschrift

Analogously to Example 1, 290 mg (0.7 mmol) of 4,5-bis(4-fluoroanilino)phthalic acid dimethyl ester in 22 ml of ethylene glycol are heated at 120° and, with stirring, ammonia gas is passed through the mixture for 18 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 hexane/ethyl acetate 1:1 and the product fractions are combined and concentrated by evaporation, yielding the title compound in the form of orange crystals, m.p.>220° C., FAB-MS: 366 [M+ +H].

Aufarbeitung

  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 hexane/ethyl acetate 1:1
  7. concentrationconcentrated by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-a07be471ebc64e9db9fafd5c664f5bfc
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05663336

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