Cyclohexylhydrazine hydrochloride → HCID 63235160, Verbindung

HRID 12893

Reaktionsgleichung

Reaktionsgleichung von HRID 12893
Cl.[CH:2]1([NH:8][NH2:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH2:10]([O:12][C:13](=[O:25])[C:14](=[CH:21]N(C)C)[C:15](=O)[C:16]([F:19])([F:18])[F:17])[CH3:11].C([O-])(=O)C.[Na+]>C(O)C>[CH2:10]([O:12][C:13]([C:14]1[CH:21]=[N:9][N:8]([CH:2]2[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2)[C:15]=1[C:16]([F:17])([F:18])[F:19])=[O:25])[CH3:11]

Komponenten

5

Edukt 3

HCID 207836Cyclohexylhydrazine hydrochlorideHCID 517045Sodium AcetateHCID 53979199Butanoic acid, 2-[(dimethylamino)methylene]-4,4,4-trifluoro-3-oxo-, ethyl ester

Produkt 1

HCID 63235160HCID 63235160, VerbindungAusbeute 58,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Cyclohexyl-hydrazine hydrochloride (0.276 g, 1.59 mmol, CAS #24214-73-1, purchased from Aldrich), 2-dimethylaminomethylene-4,4,4-trifluoro-3-oxo-butyric acid ethyl ester (0.459 g, 1.67 mmol) and anhydrous sodium acetate (0.188 g, 2.29 mmol) were combined in ethanol (2.9 mL) and heated at 70° C. for 15 hours. After cooling to room temperature, the reaction mixture was partitioned between methylene chloride and water. The organic phase was washed with water and brine. Each aqueous phase was back extracted with a second portion of methylene chloride. The two organic phases were combined, dried over sodium sulfate and concentrated in vacuo. Purification by flash chromatography, eluting with a 5-40% ethyl acetate-hexanes gradient, yielded 1-cyclohexyl-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid ethyl ester (0.270 g, 55%). Mass spectrum: m/z: 291.3 (M+H).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. customthe reaction mixture was partitioned between methylene chloride and water
  3. washThe organic phase was washed with water and brine
  4. extractionEach aqueous phase was back extracted with a second portion of methylene chloride
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography
  8. washeluting with a 5-40% ethyl acetate-hexanes

Quellen und Nachweise

ORD-Eintrag
ord-ad7362163d764e3488d83dde6ee65506
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728029B2

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