2-(Ethoxymethylene)propanedinitrile → 5-Amino-1-(2-chlorophenyl)-1H-pyrazole-4-carbonitrile

HRID 2261247ノート

反応式

HRID 2261247 の反応式
C(O[CH:4]=[C:5]([C:8]#[N:9])[C:6]#[N:7])C.Cl.[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH:18][NH2:19]>CCO>[NH2:9][C:8]1[N:18]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[Cl:11])[N:19]=[CH:4][C:5]=1[C:6]#[N:7]

参加物

4

反応物 2

HCID 671522-(Ethoxymethylene)propanedinitrileHCID 4432872-Chlorophenylhydrazine hydrochloride

生成物 1

HCID 123660385-Amino-1-(2-chlorophenyl)-1H-pyrazole-4-carbonitrile

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

At RT, 2-(ethoxymethylene)malononitrile (5.77 g, 47.2 mmol) was added in portions to a stirred suspension of 1-(2-chlorophenyl)hydrazine hydrochloride (8.05 g, 45.0 mmol) and TEA (6.58 ml, 47.2 mmol) in absolute EtOH (56 mL). The mixture was heated to reflux for 1 h. The volatile solvents were removed under reduced pressure. The brown reside was dissolved in EtOAc, washed with water followed by saturated NaHCO3 solution. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure to obtain 5-amino-1-(2-chlorophenyl)-1H-pyrazole-4-carbonitrile as a rusty crystalline solid. MS (ESI, pos.ion) m/z: 219.0 (M+1).

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1 h
  3. customThe volatile solvents were removed under reduced pressure
  4. dissolutionThe brown reside was dissolved in EtOAc
  5. washwashed with water
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-7319fc4a052d47338e9434a11088332f
出典データセット
uspto-grants-2010_12
特許番号
US07846944B2

反応ノート

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