Cyclohexylhydrazine hydrochloride → HCID 63235160, 화합물

HRID 12893

반응식

HRID 12893 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

HCID 63235160HCID 63235160, 화합물수율 58.5%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
70 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ad7362163d764e3488d83dde6ee65506
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728029B2

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