Pentanenitrile, 4,4-dimethyl-3-oxo- → 3-tert-Butyl-1-(3,4-dimethylphenyl)-1H-pyrazol-5-amine

HRID 60625

Reaktionsgleichung

Reaktionsgleichung von HRID 60625
Cl.[CH3:2][C:3]1[CH:4]=[C:5]([NH:10][NH2:11])[CH:6]=[CH:7][C:8]=1[CH3:9].[CH3:12][C:13]([CH3:20])([CH3:19])[C:14](=O)[CH2:15][C:16]#[N:17]>CCO>[C:13]([C:14]1[CH:15]=[C:16]([NH2:17])[N:10]([C:5]2[CH:6]=[CH:7][C:8]([CH3:9])=[C:3]([CH3:2])[CH:4]=2)[N:11]=1)([CH3:20])([CH3:19])[CH3:12]

Komponenten

4

Edukt 2

HCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 1737401-(3,4-Dimethylphenyl)hydrazine hydrochloride

Produkt 1

HCID 108685003-tert-Butyl-1-(3,4-dimethylphenyl)-1H-pyrazol-5-amineAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A black solution of 3,4-dimethylphenyl hydrazine hydrochloride (Apollo, 1.73 g, 10.0 mmol) and 4,4-dimethyl-3-oxopentanenitrile (1.38 g, 11.0 mmol) in EtOH (20 mL) was stirred at reflux for 5 h. The cooled solution was concentrated in vacuo, redissolved in diethyl ether (20 mL) and washed with aqueous NaOH solution (1M, 20 mL). The aqueous was extracted with diethyl ether (2×20 mL), then the combined organics washed with brine (20 mL), dried (Na2SO4), filtered and concentrated in vacuo to leave the title compound (2.18 g, 90%). LCMS (Method 3): Rt 2.75 min, m/z 244 [MH+].

Aufarbeitung

  1. temperatureat reflux for 5 h
  2. concentrationThe cooled solution was concentrated in vacuo
  3. dissolutionredissolved in diethyl ether (20 mL)
  4. washwashed with aqueous NaOH solution (1M, 20 mL)
  5. extractionThe aqueous was extracted with diethyl ether (2×20 mL)
  6. washthe combined organics washed with brine (20 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ae397177b3734a19acc85476d8e9d6ce
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440974B2

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