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Triethylamine → 5-amino-1-isopropyl-1H-pyrazole-4-carbonitrile

HRID 1093182
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1093182
C(O[CH:4]=[C:5]([C:10]#[N:11])[CH:6](O)C#N)C.[CH:12]([NH:15][NH2:16])([CH3:14])[CH3:13].C([N:19](CC)CC)C>C(O)C>[NH2:11][C:10]1[N:15]([CH:12]([CH3:14])[CH3:13])[N:16]=[CH:4][C:5]=1[C:6]#[N:19]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 527891-IsopropylhydrazineHCID 539932842-(Ethoxymethylidene)-3-hydroxybutanedinitrile

Produkt 1

HCID 179620285-amino-1-isopropyl-1H-pyrazole-4-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A mixture of ethoxymethylenemalonitrile (0.55 g, 4.5 mmol) and iso-propylhydrazine (0.50 g, 4.5 mmol) in ethanol (10 mL) in a 10-20 mL Smith process vial was treated with triethylamine (0.88 mL). The vial was capped and heated in the microwave reactor for one hour at 150° C. Following cooling of the vial, the mixture was concentrated to dryness under reduced pressure. The residue was partitioned between ethyl acetate and water. The aqueous phase was extracted with ethyl acetate. The combined organic extracts were washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and concentrated to dryness under reduced pressure to provide 5-amino-1-isopropyl-1H-pyrazole-4-carbonitrile as a slowly solidifying syrup (0.72 g, >100%). MS (ES+): 151.2 (M+H)+

Aufarbeitung

  1. customThe vial was capped
  2. temperatureFollowing cooling of the vial, the mixture
  3. concentrationwas concentrated to dryness under reduced pressure
  4. customThe residue was partitioned between ethyl acetate and water
  5. extractionThe aqueous phase was extracted with ethyl acetate
  6. washThe combined organic extracts were washed with saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7052b498e7794d859fe77d82bbf3f783
Quelldatensatz
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08129371B2

Notizen zur Reaktion

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