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Cyclopropylamine → HCID 13579376, Verbindung

HRID 1589081
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1589081
[C:1]1([CH:7]2[C:11](=[O:12])[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=3)=[C:9]([NH2:23])[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:24]1(N)[CH2:26][CH2:25]1>C(O)C>[C:1]1([CH:7]2[C:11](=[O:12])[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:20])([F:21])[F:22])[CH:14]=3)=[C:9]([NH:23][CH:24]3[CH2:26][CH2:25]3)[O:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 69828Cyclopropylamine2×HCID 13579285HCID 13579285, Verbindung

Produkt 1

HCID 13579376HCID 13579376, VerbindungAusbeute 36,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

In this example, a mixture containing 5.0 g (0.0157 g mole) of 2-phenyl-3-oxo-4-(3-trifluoromethylphenyl)-5-amino-2,3-dihydrofuran and 8.96 g of cyclopropylamine in 50 ml of ethanol containing 5% water was refluxed for six days. At the end of this time, a sample of the reaction mixture was checked by thin layer chromatography and then an additional 8.96 g of cyclopropylamine was added. The mixture was refluxed for an additional 24 hours and then allowed to stand at room temperature over night. The mixture was then concentrated by evaporation under vacuum, affording a crude product oil. The crude product was chromatographed over silica gel eluting with 80:20 (V/V) petroleum ether and ethyl acetate. The product fractions were combined and evaporated in vacuo affording 2.07 g of the title compound Elemental Analysis Carbon calc.: 66.8%, found 67.4%; hydrogen calc.: 4.5%, found 4.7%; nitrogen calc.: 3.9%, found 4.6%; melting point 160°-164° C.

Aufarbeitung

  1. temperaturewas refluxed for six days
  2. temperatureThe mixture was refluxed for an additional 24 hours
  3. waitto stand at room temperature over night
  4. concentrationThe mixture was then concentrated by evaporation under vacuum
  5. customaffording a crude product oil
  6. customThe crude product was chromatographed over silica gel eluting with 80:20 (V/V) petroleum ether and ethyl acetate
  7. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-36a69d75279c47b39577b0c812143b03
Quelldatensatz
uspto-grants-1986_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04568378

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