Pentanenitrile, 4,4-dimethyl-3-oxo- → 4-(5-Amino-3-tert-butyl-1H-pyrazol-1-yl)benzonitrile

HRID 75591Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 75591
Cl.[C:2]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][NH2:11])=[CH:6][CH:5]=1)#[N:3].[CH3:12][C:13]([CH3:20])([CH3:19])[C:14](=O)[CH2:15][C:16]#[N:17]>CCO>[NH2:17][C:16]1[N:10]([C:7]2[CH:8]=[CH:9][C:4]([C:2]#[N:3])=[CH:5][CH:6]=2)[N:11]=[C:14]([C:13]([CH3:20])([CH3:19])[CH3:12])[CH:15]=1

Komponenten

4

Edukt 2

HCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 162129624-Cyanophenylhydrazine Hydrochloride

Produkt 1

HCID 71470834-(5-Amino-3-tert-butyl-1H-pyrazol-1-yl)benzonitrileAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A cream suspension of 4-cyanophenylhydrazine hydrochloride (1.70 g, 10.0 mmol) and 4,4-dimethyl-3-oxopentanenitrile (1.31 g, 10.5 mmol) in EtOH (25 mL) was stirred at reflux for 4 h, then at RT for 64 h, and again at reflux for 24 h. The solution was cooled to RT, concentrated in vacuo, and partitioned between water (50 mL) and EtOAc (75 mL). The organics were washed with brine (50 mL), dried (Na2SO4), filtered and concentrated in vacuo to leave an orange solid (2.28 g, 95%). LCMS (Method 3): Rt 3.45 min, m/z 241 [MH+].

Aufarbeitung

  1. temperatureat reflux for 4 h
  2. temperatureagain at reflux for 24 h
  3. concentrationconcentrated in vacuo
  4. custompartitioned between water (50 mL) and EtOAc (75 mL)
  5. washThe organics were washed with brine (50 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f981191d6d004772bb16d33b65bafe56
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835431B2

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