Cyclopropylamine → HCID 178471879, Verbindung

HRID 1440097

Reaktionsgleichung

Reaktionsgleichung von HRID 1440097
[CH:1]([O-:6])([O-])[O:2][CH2:3][CH3:4].[F:7][CH:8]([F:27])[O:9][C:10]1[C:11]([F:26])=[C:12]([CH:21]=[C:22]([F:25])[C:23]=1[F:24])[C:13]([CH2:15][C:16](OCC)=O)=[O:14].[CH:28]1([NH2:31])[CH2:30][CH2:29]1>C(OC(=O)C)(=O)C>[CH:28]1([NH:31][CH:16]=[C:15]([C:13](=[O:14])[C:12]2[CH:21]=[C:22]([F:25])[C:23]([F:24])=[C:10]([O:9][CH:8]([F:7])[F:27])[C:11]=2[F:26])[C:1]([O:2][CH2:3][CH3:4])=[O:6])[CH2:30][CH2:29]1

Komponenten

5

Edukt 3

HCID 69828CyclopropylamineHCID 15023784Ethyl 3-difluoromethoxy-2,4,5-trifluorobenzoylacetateHCID 53630039Ethylorthoformate

Produkt 1

HCID 178471879HCID 178471879, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7918Acetic AnhydrideLösungsmittel

Versuchsvorschrift

20 ml of acetic anhydride and 6 ml of ethyl orthoformate were added to the whole of the ethyl 3-difluoromethoxy-2,4,5-trifluorobenzoylacetate [(XV), R1 =--OCHF2, R3' =H, R17 =C2H5, X=X'=F] prepared as described in step (b) above, and, after the mixture had been heated under reflux for 2 hours, the excess acetic anhydride and ethyl orthoformate were removed by evaporation under reduced pressure. The residue was dissolved in 200 ml of methylene chloride, and 1.25 g (0.022 moles) of cyclopropylamine was added dropwise, whilst stirring and ice-cooling; the stirring was continued, whilst ice-cooling, for an additional 1 hour. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure, and the residue was subjected to silica gel column chromatography, using a 9:1 by volume mixture of toluene and ethyl acetate as the eluent, to give 3.29 g of ethyl 3-cyclopropylamino-2-(3-difluoromethoxy-2,4,5trifluorobenzoyl)acrylate as an amber colored liquid.

Aufarbeitung

  1. custom' =H, R17 =C2H5, X=X'=F] prepared
  2. temperaturehad been heated
  3. temperatureunder reflux for 2 hours
  4. customthe excess acetic anhydride and ethyl orthoformate were removed by evaporation under reduced pressure
  5. dissolutionThe residue was dissolved in 200 ml of methylene chloride
  6. temperatureice-cooling
  7. temperaturecooling, for an additional 1 hour
  8. concentrationAt the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure
  9. additionby volume mixture of toluene and ethyl acetate as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-896356d07504453a9cf83c06b2858d86
Quelldatensatz
uspto-grants-1996_03
Patentnummer
US05496951

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