2-Propenoic acid, 2-cyano-3-ethoxy-, ethyl ester → ethyl 5-amino-1-cyclohexyl-1H-pyrazole-4-carboxylate

HRID 1693493

反応式

HRID 1693493 の反応式
Cl.[CH:2]1([NH:8][NH2:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH2:10]([O:12][C:13](=[O:21])[C:14]([C:19]#[N:20])=[CH:15]OCC)[CH3:11].C(=O)(O)[O-].[Na+]>C(O)C>[CH2:10]([O:12][C:13]([C:14]1[CH:15]=[N:9][N:8]([CH:2]2[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2)[C:19]=1[NH2:20])=[O:21])[CH3:11]

参加物

5

反応物 3

HCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl esterHCID 207836Cyclohexylhydrazine hydrochlorideHCID 516892Sodium Bicarbonate

生成物 1

HCID 351028ethyl 5-amino-1-cyclohexyl-1H-pyrazole-4-carboxylate

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
80 °C

実験手順

To a round bottom flask is added cyclohexyl-hydrazine hydrochloride (4.5 g, 30 mmol), 2-cyano-3-ethoxy-acrylic acid ethyl ester (5.1 g, 30 mmol), sodium bicarbonate (2.6 g, 30.9 mmol) and 40 mL of ethanol. The mixture is heated to 80° C. for 1 hour, cooled down to room temperature and concentrated. The residue is dissolved in chloroform and washed with water, dried over sodium sulfate. After removal of the solvent, the solid is recrystallized from ethyl acetate: 1HNMR (CDCl3): δ 7.40 (1 H, s), 4.77 (2 H, brs), 4.05 (2 H, q, J=7.2 Hz), 3.50 (1 H, m), 1.61-1.71 (6 H, m), 1.50 (1 H, m), 1.02-1.21 (3 H, m), 1.13 (3 H, t, J=7.2 Hz).

後処理

  1. temperaturecooled down to room temperature
  2. concentrationconcentrated
  3. dissolutionThe residue is dissolved in chloroform
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. customAfter removal of the solvent
  7. customthe solid is recrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-07328134611a46d4b3c645e6659a2193
出典データセット
uspto-grants-2012_04
特許番号
US08158634B2

関連ノート

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