Triethylamine → ethyl 5-amino-1-ethyl-1H-pyrazole-4-carboxylate

HRID 220941

反応式

HRID 220941 の反応式
C(N(CC)CC)C.C(O[CH:11]=[C:12]([C:18]#[N:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14])C.C(O)(=O)C(O)=O.[CH2:26]([NH:28][NH2:29])[CH3:27]>C(O)C>[CH2:16]([O:15][C:13]([C:12]1[CH:11]=[N:29][N:28]([CH2:26][CH3:27])[C:18]=1[NH2:19])=[O:14])[CH3:17]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl esterHCID 96181Hydrazine, ethyl-, ethanedioate (1:1)

生成物 1

HCID 15192649ethyl 5-amino-1-ethyl-1H-pyrazole-4-carboxylate収率 80.1%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Triethylamine (19.6 ml, 144 mmol) was added cautiously to a solution of ethyl (ethoxymethylene)cyanoacetate (10.1 g, 60 mmol) and ethyl hydrazine oxalate (9.9 g, 66 mmol) in ethanol (200 ml). The mixture was heated at reflux for 24 h then concentrated in vacuo. The residue was redissolved in EtOAc, washed with 5% KHCO3 solution then brine, dried and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; 25% pet. ether:75% EtOAc) to yield the title compound (8.8 g, 80%).

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 24 h
  3. concentrationthen concentrated in vacuo
  4. dissolutionThe residue was redissolved in EtOAc
  5. washwashed with 5% KHCO3 solution
  6. dry with materialbrine, dried
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography on silica gel (eluant; 25% pet. ether:75% EtOAc)

出典と根拠

ORDレコード
ord-3d79a6c5618a4960a925aeae8f102cd0
出典データセット
uspto-grants-2012_06
特許番号
US08202858B2

関連ノート

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