Hydrazine hydrate (1:1) → 3-(n-Butyl)-5,5-dimethyl-4-phenyl-4,5-dihydropyrazole

HRID 1958564Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1958564
[CH3:1][C:2](=[C:4]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5](=O)[CH2:6][CH2:7][CH2:8][CH3:9])[CH3:3].[NH2:17][NH2:18].O>C(O)C>[CH2:6]([C:5]1[CH:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:2]([CH3:3])([CH3:1])[NH:18][N:17]=1)[CH2:7][CH2:8][CH3:9]

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 59864949HCID 59864949, Verbindung

Produkt 1

HCID 598649343-(n-Butyl)-5,5-dimethyl-4-phenyl-4,5-dihydropyrazoleAusbeute 98,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a magnetically stirred solution of 2-methyl-3-phenyloct-2-en-4-one (Intermediate III-1) (1.96 gram, 9.07 mmol) in absolute ethanol (15 ml) was added hydrazine.hydrate (0.88 ml, 18.14 mmol) and the resulting solution was heated at reflux temperature for 4 hours under a nitrogen atmosphere. The resulting solution was allowed to attain room temperature, concentrated and taken up in a mixture of MTBE and water. The organic layer was collected, dried over MgSO4, filtered and concentrated to give crude 3-(n-butyl)-5,5-dimethyl-4-phenyl-4,5-dihydropyrazole (Intermediate IV-1) (2.06 gram) as an oil. 1H-NMR (400 MHz, CDCl3) δ 0.80-0.89 (m, 6H), 1.23-1.37 (m, 5H), 1.42-1.54 (m, 2H), 2.06-2.35 (m, 2H), 3.52 (s, 1H), 4.90 (br s, 1H), 7.07 (br d, J˜8 Hz, 2H), 7.19-7.38 (m, 3H).

Aufarbeitung

  1. temperaturethe resulting solution was heated
  2. temperatureat reflux temperature for 4 hours under a nitrogen atmosphere
  3. customto attain room temperature
  4. concentrationconcentrated
  5. additiontaken up in a mixture of MTBE and water
  6. customThe organic layer was collected
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-54cef5995bb7423181abf71625fcc10e
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08410135B2

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