Hydrochloric Acid → 1-Phenyl-5-(3-propylphenyl)-4,5-dihydro-1H-pyrazol-3-ylamine

HRID 83514ノート

反応式

HRID 83514 の反応式
[O-]CC.[Na+].[C:5]1([NH:11][NH2:12])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH2:13]([C:16]1[CH:17]=[C:18](/[CH:22]=[CH:23]/[C:24]#[N:25])[CH:19]=[CH:20][CH:21]=1)[CH2:14][CH3:15].C(C1C=C(/C=C\C#N)C=CC=1)CC.Cl>C(O)C.O>[C:5]1([N:11]2[CH:22]([C:18]3[CH:19]=[CH:20][CH:21]=[C:16]([CH2:13][CH2:14][CH3:15])[CH:17]=3)[CH2:23][C:24]([NH2:25])=[N:12]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 7516PhenylhydrazineHCID 2723922Sodium ethoxideHCID 86680356HCID 86680356、化合物HCID 86680357(Z)-3-(3-propylphenyl)acrylonitrile

生成物 1

HCID 712877421-Phenyl-5-(3-propylphenyl)-4,5-dihydro-1H-pyrazol-3-ylamine

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒2 回HCID 962Water溶媒

実験手順

To a solution of sodium ethoxide (20 wt % in ethanol, 31 ml) in ethanol (66 ml) was stirred and added dropwise phenylhydrazine (6.4 ml) at room temperature, and then the mixture was stirred for 40 minutes. To this reaction solution was added dropwise a solution of the mixture of (E)-3-(3-propylphenyl)acrylonitrile and (Z)-3-(3-propylphenyl)acrylonitrile (11.1 g) in ethanol (33 ml), and then the mixture was stirred overnight at reflux. This reaction solution was cooled to room temperature, and water (30 ml) was added thereto. Next, pH of the reaction solution was adjusted to 7 by adding a 6M aqueous solution of hydrochloric acid under ice-cooling. This mixed solution was extracted with ethyl acetate, and the resulting organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. To the resulting residue was added toluene, and the mixture was dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. To the resulting residue was added toluene, and again concentrated under reduced pressure to give a crude product of the titled compound (18.6 g).

後処理

  1. additionTo this reaction solution was added dropwise
  2. stirringthe mixture was stirred overnight
  3. temperatureat reflux
  4. temperaturecooling
  5. extractionThis mixed solution was extracted with ethyl acetate
  6. washthe resulting organic layer was washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. additionTo the resulting residue was added toluene
  10. dry with materialthe mixture was dried over anhydrous magnesium sulfate
  11. concentrationconcentrated under reduced pressure
  12. additionTo the resulting residue was added toluene
  13. concentrationagain concentrated under reduced pressure

出典と根拠

ORDレコード
ord-dfd95f5b4fa94cc99ba47c368a7d0de0
出典データセット
uspto-grants-2014_09
特許番号
US08846746B2

反応ノート

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