Cyclohexylhydrazine hydrochloride → HCID 63235160, compound

HRID 12893

Reaction equation

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]

Participants

Conditions

Temperature: 70 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-ad7362163d764e3488d83dde6ee65506
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07728029B2

Linked notes

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