Acetic Anhydride → HCID 178471869, Verbindung

HRID 47891Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 47891
[C:1]([C:3]1[C:4]([Cl:19])=[C:5]([CH:14]=[C:15]([F:18])[C:16]=1[Cl:17])[C:6]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:7])#[N:2].[CH:20](OCC)(OCC)OCC.C(OC(=O)C)(=O)C.[CH:37]1([NH2:40])[CH2:39][CH2:38]1>>[C:1]([C:3]1[C:4]([Cl:19])=[C:5]([CH:14]=[C:15]([F:18])[C:16]=1[Cl:17])[C:6]([C:8](=[CH:20][NH:40][CH:37]1[CH2:39][CH2:38]1)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:7])#[N:2]

Komponenten

5

Edukt 4

HCID 7918Acetic AnhydrideHCID 31214Ethyl orthoformateHCID 69828CyclopropylamineHCID 86589175Ethyl 3-cyano-2,4-dichloro-5-fluorobenzoylacetate

Produkt 1

HCID 178471869HCID 178471869, VerbindungAusbeute 70,1 %

Versuchsvorschrift

76.0 g of ethyl 3-cyano-2,4-dichloro-5-fluorobenzoylacetate (0.25 mol), 66.6 g of triethyl orthoformate (0.45 mol) and 77.4 g of diacetyl oxide (0.72 mol) were stirred at 150° C. for 2.5 hours. Fractions having a lower boiling point were evaporated under reduced pressure. To the residue was added 250 ml of anhydrous ethanol. 14.5 g of cyclopropylamine (0.25 mol) was added to the solution and the reaction was then carried out for 2 hours. The resulting mixture was filtered under suction. The residue was recrystallized from a mixture of petroleum ether and cyclohexane to yield 65.0 g (0.175 mol) of ethyl 2-(3-cyano-2,4-dichloro-5-fluorobenzoyl)-3-cyclopropylaminoacrylate in 70.1% yield.

Aufarbeitung

  1. customwere evaporated under reduced pressure
  2. additionTo the residue was added 250 ml of anhydrous ethanol
  3. filtrationThe resulting mixture was filtered under suction
  4. customThe residue was recrystallized from a mixture of petroleum ether and cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-670782c6bd174e549333fde5e909bd54
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06699992B2

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