Cyclopentylhydrazine hydrochloride → 1-cyclopentyl-3-phenylmethyl-4-cyano-5-amino-1H-pyrazole

HRID 1736555

反応式

HRID 1736555 の反応式
Cl.[CH:2]1([NH:7][NH2:8])[CH2:6][CH2:5][CH2:4][CH2:3]1.C[O-].[Na+].CO[C:14]1([CH2:20][CH:21]=[C:22]([C:25]#[N:26])[C:23]#[N:24])[CH:19]=[CH:18][CH:17]=[CH:16][CH2:15]1>C(O)C>[CH:2]1([N:7]2[C:25]([NH2:26])=[C:22]([C:23]#[N:24])[C:21]([CH2:20][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:8]2)[CH2:6][CH2:5][CH2:4][CH2:3]1

参加物

5

反応物 3

HCID 212349Cyclopentylhydrazine hydrochlorideHCID 10942334Sodium MethoxideHCID 86747657(1-Methoxyphenylethylidene)malononitrile

生成物 1

HCID 218309241-cyclopentyl-3-phenylmethyl-4-cyano-5-amino-1H-pyrazole収率 26%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

実験手順

A mixture of cyclopentyl hydrazine hydrochloride (1.4 g, 10.2 mmol), sodium methoxide (0.55 g, 10.2 mmol) and ethanol (30 ml) was heated to reflux and then (1-methoxyphenylethylidene)malononitrile (2.0 g, 10.2 mmol) in ethanol (15 ml) was added dropwise over 1 hour. The reaction mixture was refluxed for 6.5 hours and the solvent was removed in vacuo. The residue was partitioned between chloroform and water, the organic layer was separated and the aqueous layer was extracted with chloroform (3×75 ml). The combined organic layers were washed with brine, dried over anhydrous MgSO4 and concentrated in vacuo to afford 0.7 g (26%) of 1-cyclopentyl-3-phenylmethyl-5-amino-1H-pyrazole-4-carbonitrile as white flakes, m.p. 180°-182° C. when recrystallized from ethyl acetate and dried for 18 hours at 90° C. in high vacuum.

後処理

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperatureThe reaction mixture was refluxed for 6.5 hours
  4. customthe solvent was removed in vacuo
  5. customThe residue was partitioned between chloroform and water
  6. customthe organic layer was separated
  7. extractionthe aqueous layer was extracted with chloroform (3×75 ml)
  8. washThe combined organic layers were washed with brine
  9. dry with materialdried over anhydrous MgSO4
  10. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-162bb1cec3ac403caa1b9a7b7b3b9023
出典データセット
uspto-grants-1996_07
特許番号
US05541187

関連ノート

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