Reaktionsgleichung
Cl.[CH:2]1([NH:8][NH2:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.C(O[CH:13]=[C:14]([C:20]#[N:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16])C.C([O-])(=O)C.[Na+]>C(O)C>[CH2:18]([O:17][C:15]([C:14]1[CH:13]=[N:9][N:8]([CH:2]2[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2)[C:20]=1[NH2:21])=[O:16])[CH3:19]Komponenten
Reaktionsbedingungen
- Temperatur
- 70 °C
Versuchsvorschrift
Cyclohexylhydrazine hydrochloride (3.057 g, 20.29 mmol, CAS #24214-73-1, purchased from Aldrich) was combined with ethyl (ethoxymethylene)-cyanoacetate (3.390 g, 20.04 mmol) and anhydrous sodium acetate (2.080 g, 25.36 mmol) in 30 mL ethanol. The mixture was heated at 70° C. for 16 hours then cooled to room temperature and concentrated. The residue was partitioned between methylene chloride and water. The separated aqueous phase was extracted with a second portion of methylene chloride. The organic phases were successively washed with water and brine and then combined, dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography eluting with a gradient of 25-70% ethyl acetate/hexanes to give 5-amino-1-cyclohexyl-1H-pyrazole-4-carboxylic acid ethyl ester (4.42 g, 92%). Mass spectrum: m/z: 238.1 (M+H).
Aufarbeitung
- temperaturethen cooled to room temperature
- concentrationconcentrated
- customThe residue was partitioned between methylene chloride and water
- extractionThe separated aqueous phase was extracted with a second portion of methylene chloride
- washThe organic phases were successively washed with water and brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuo
- customThe residue was purified by flash chromatography
- washeluting with a gradient of 25-70% ethyl acetate/hexanes
Quellen und Nachweise
- ORD-Eintrag
- ord-5ca9e47eaaeb489c8850e026eadd480c
- Quelldatensatz
- uspto-grants-2010_06
- Patentnummer
- US07728029B2
Verknüpfte Notizen
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