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Potassium Carbonate → 6-(Trifluoromethyl)-4,5-dihydropyridazin-3(2H)-one

HRID 877221
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 877221
O=C1O[C:5]([CH2:11][CH2:12][C:13]([O:15]C(C)(C)C)=O)([C:7]([F:10])([F:9])[F:8])[N:4]=C1C(C)C.Cl.[NH2:24]N.C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C.O>[F:8][C:7]([F:10])([F:9])[C:5]1[CH2:11][CH2:12][C:13](=[O:15])[NH:24][N:4]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 115031Hydrazinium chlorideHCID 66933100HCID 66933100, Verbindung

Produkt 1

HCID 497606526-(Trifluoromethyl)-4,5-dihydropyridazin-3(2H)-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962
Water
Lösungsmittel

Versuchsvorschrift

8.44 g (26.1 mmol) of tert-butyl 3-[5-oxo-4-(propan-2-yl)-2-(trifluoromethyl)-2,5-dihydro-1,3-oxazol-2-yl]propanoate [CAS Reg. No. 87341-14-8] and 13.44 g (130.5 mmol) of hydrazine hydrochloride were stirred in 100 ml of glacial acetic acid at 118° C. for 2 hours. The reaction solution was then evaporated to dryness under reduced pressure. The residue obtained was taken up in 100 ml of water and made basic using potassium carbonate. The basic solution was subsequently extracted three times with dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered and concentrated to dryness. The crude product was purified chromatographically on silica gel (mobile phase dichloromethane/methanol 50:1→10:1). This gave 2.65 g (15.95 mmol, 61% of theory) of the title compound.

Aufarbeitung

  1. customThe reaction solution was then evaporated to dryness under reduced pressure
  2. customThe residue obtained
  3. extractionThe basic solution was subsequently extracted three times with dichloromethane
  4. dry with materialThe combined organic phases were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe crude product was purified chromatographically on silica gel (mobile phase dichloromethane/methanol 50:1→10:1)

Quellen und Nachweise

ORD-Eintrag
ord-86a42abebece464fb4a459107c6e36bb
Quelldatensatz
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08987256B2

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