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Sodium hydride → Ethyl 3-amino-2-(2-oxopentyl)pyrazol-4-carboxylate

HRID 274565
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 274565
[H-].[Na+].[NH2:3][C:4]1[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:7][NH:6][N:5]=1.Br[CH2:15][C:16](=[O:20])[CH2:17][CH2:18][CH3:19]>CN(C=O)C>[NH2:3][C:4]1[N:5]([CH2:15][C:16](=[O:20])[CH2:17][CH2:18][CH3:19])[N:6]=[CH:7][C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 100578691-Bromopentan-2-oneHCID 178469928HCID 178469928, Verbindung

Produkt 1

HCID 20092995Ethyl 3-amino-2-(2-oxopentyl)pyrazol-4-carboxylateAusbeute 45,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of sodium hydride (60% dispersion in mineral oil, 0.8 g) in DMF (50 ml) was added ethyl 3-amino-pyrazol-4-carboxylate (2.0 g) and the reaction mixture was stirred at room temperature for 15 minutes. After addition of 1-bromo-2-pentanone (4.0 g), the mixture was stirred at room temperature for 13 hours. The reaction mixture was concentrated to dryness, and the residue was dissolved in ethyl acetate-water. The organic layer was washed with water, dried and concentrated to dryness. The resulting yellow syrup was purified by column chromatography on silica gel to give pale yellow prisms (1.4 g, 45%).

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 13 hours
  2. concentrationThe reaction mixture was concentrated to dryness
  3. dissolutionthe residue was dissolved in ethyl acetate-water
  4. washThe organic layer was washed with water
  5. customdried
  6. concentrationconcentrated to dryness
  7. customThe resulting yellow syrup was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-f983fe279efb4c8381f2729c0fd64fb7
Quelldatensatz
uspto-grants-1995_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05389641

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