Phenylhydrazine hydrochloride → ethyl 1-phenyl-5-(2,4,5-trifluorophenyl)-1H-pyrazole-4-carboxylate

HRID 402759

反応式

HRID 402759 の反応式
O=[C:2]([C:9]1[CH:14]=[C:13]([F:15])[C:12]([F:16])=[CH:11][C:10]=1[F:17])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].COC(OC)[N:21]([CH3:23])C.Cl.[C:27]1([NH:33]N)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(O)C.CCOC(C)=O>[C:27]1([N:33]2[C:2]([C:9]3[CH:14]=[C:13]([F:15])[C:12]([F:16])=[CH:11][C:10]=3[F:17])=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH:23]=[N:21]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

参加物

6

反応物 3

HCID 60962Phenylhydrazine hydrochlorideHCID 78373Dimethylformamide dimethyl acetalHCID 2758933Ethyl 2,4,5-trifluorobenzoylacetate

生成物 1

HCID 86685264ethyl 1-phenyl-5-(2,4,5-trifluorophenyl)-1H-pyrazole-4-carboxylate

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of ethyl 3-oxo-3-(2,4,5-trifluorophenyl)propanoate (0.326 g, 1.32 mmol) and N,N-dimethyformamide dimethyl acetal in ethanol (5 mL) was heated in a 90° C. oil bath for 3 hours. Upon removal of the volatiles, the residue was dissolved in EtOH (3 mL) and phenylhydrazine hydrochloride salt (191 mg, 1.324 mmol) was added. The mixture was then heated at reflux for 6 hours. The reaction was cooled and diluted with EtOAc and the organic layer was washed with NaHCO3 and brine. The organic phase was dried with Na2SO4, filtered and concentrated to afford the title compound as oil.

後処理

  1. customUpon removal of the volatiles
  2. dissolutionthe residue was dissolved in EtOH (3 mL)
  3. temperatureThe mixture was then heated
  4. temperatureat reflux for 6 hours
  5. temperatureThe reaction was cooled
  6. washthe organic layer was washed with NaHCO3 and brine
  7. dry with materialThe organic phase was dried with Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-2c3f4e2ed52c445c8ea94ce06b9794be
出典データセット
uspto-grants-2014_06
特許番号
US08742110B2

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