Methyl iodide → HCID 22610929, Verbindung

HRID 840528

Reaktionsgleichung

Reaktionsgleichung von HRID 840528
C(O[C:4](=[O:12])[CH:5]=[C:6]([NH2:11])[C:7]([F:10])([F:9])[F:8])C.[H-].[Na+].[H][H].C([O:19][C:20]([NH:22][C:23]1[C:28]([F:29])=[CH:27][C:26]([Cl:30])=[CH:25][N:24]=1)=O)C.[CH3:31]I>CN1CCCC1.C(OCC)(=O)C>[F:29][C:28]1[C:23]([N:22]2[C:4](=[O:12])[CH:5]=[C:6]([C:7]([F:8])([F:9])[F:10])[N:11]([CH3:31])[C:20]2=[O:19])=[N:24][CH:25]=[C:26]([Cl:30])[CH:27]=1

Komponenten

8

Edukt 5

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 136209Ethyl 3-amino-4,4,4-trifluoro-2-butenoateHCID 226109302-Ethoxycarbonylamino-3-fluoro-5-chloropyridineHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 22610929HCID 22610929, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 84541-MethylpyrrolidineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Under a nitrogen atmosphere, while cooling and stirring, a solution of 22.7 g 4,4,4-trifluoro-3-amino-2-butenoic acid ethyl ester is added dropwise to 5.1 g of a sodium hydride dispersion (60%) in 60 ml N-methylpyrrolidine at 0-5° C. and stirred at 22° C. until hydrogen evolution is complete. Then 23.7 g 2-ethoxicarbonylamino-3-fluoro-5-chloropyridine (Example H1) is added and the reaction mixture heated for about 5 hours to 120° C. The mixture is then cooled, 16.7 g methyl iodide is added dropwise and stirring is continued overnight at 22° C. After the reaction mixture has been taken up in ethyl acetate, it is washed with ice water, dried over sodium sulfate, filtered, and concentrated by evaporation. The residue obtained is recrystallized from ethyl acetate/n-hexane. The title compound is obtained with a melting point of 133-134° C.

Aufarbeitung

  1. temperatureUnder a nitrogen atmosphere, while cooling
  2. temperaturethe reaction mixture heated for about 5 hours to 120° C
  3. temperatureThe mixture is then cooled
  4. stirringstirring
  5. washit is washed with ice water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation
  9. customThe residue obtained
  10. customis recrystallized from ethyl acetate/n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-3dfbdfd7f56740fe8ffc76e0afe2a60c
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06369002B1

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