Pentanenitrile, 4,4-dimethyl-3-oxo- → 4-(5-Amino-3-tert-butyl-1H-pyrazol-1-yl)benzonitrile

HRID 572081ノート

反応式

HRID 572081 の反応式
Cl.[C:2]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][NH2:11])=[CH:6][CH:5]=1)#[N:3].[CH3:12][C:13]([CH3:20])([CH3:19])[C:14](=O)[CH2:15][C:16]#[N:17]>CCO>[NH2:17][C:16]1[N:10]([C:7]2[CH:8]=[CH:9][C:4]([C:2]#[N:3])=[CH:5][CH:6]=2)[N:11]=[C:14]([C:13]([CH3:20])([CH3:19])[CH3:12])[CH:15]=1

参加物

4

反応物 2

HCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 162129624-Cyanophenylhydrazine Hydrochloride

生成物 1

HCID 71470834-(5-Amino-3-tert-butyl-1H-pyrazol-1-yl)benzonitrile収率 95%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A cream suspension of 4-cyanophenylhydrazine hydrochloride (1.70 g, 10.0 mmol) and 4,4-dimethyl-3-oxopentanenitrile (1.31 g, 10.5 mmol) in EtOH (25 mL) was stirred at reflux for 4 h, then at RT for 64 h, and again at reflux for 24 h. The solution was cooled to RT, concentrated in vacuo, and partitioned between water (50 mL) and EtOAc (75 mL). The organics were washed with brine (50 mL), dried (Na2SO4), filtered and concentrated in vacuo to leave an orange solid (2.28 g, 95%). LCMS (Method 3): Rt 3.45 min, m/z 241 [MH+].

後処理

  1. temperatureat reflux for 4 h
  2. temperatureagain at reflux for 24 h
  3. concentrationconcentrated in vacuo
  4. custompartitioned between water (50 mL) and EtOAc (75 mL)
  5. washThe organics were washed with brine (50 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-db7d8b94b3954f1daa93a4e6b5457443
出典データセット
uspto-grants-2015_05
特許番号
US09029373B2

反応ノート

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