Ethanol → Ethyl 1H-benzimidazole-6-carboxylate

HRID 398348

反応式

HRID 398348 の反応式
[N:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([OH:12])=[O:11])=[CH:9][C:4]=2[NH:3][CH:2]=1.OS(O)(=O)=O.[CH3:18][CH2:19]O>>[CH2:18]([O:11][C:10]([C:8]1[CH:7]=[CH:6][C:5]2[N:1]=[CH:2][NH:3][C:4]=2[CH:9]=1)=[O:12])[CH3:19]

参加物

4

反応物 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 4594565-Benzimidazolecarboxylic acid

生成物 1

HCID 13505555Ethyl 1H-benzimidazole-6-carboxylate

反応条件

温度
60 °C

実験手順

To a stirred solution of benzimidazole-5-carboxylic acid (Aldrich, 10 g, 61.7 mmol) in EtOH (200 mL) was added dropwise conc. H2SO4 (8 mL), and the solution was heated to reflux. After 1 h the solution was cooled to 60° C. and stirred for 16 h. The solution was then concentrated in vacuo and the residue was partitioned between EtOAc and saturated Na2CO3 solution. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4), and concentrated in vacuo to afford the title compound as a brown solid:

後処理

  1. temperaturethe solution was heated to reflux
  2. concentrationThe solution was then concentrated in vacuo
  3. customthe residue was partitioned between EtOAc and saturated Na2CO3 solution
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with EtOAc
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-27619c151b3c40abbd63e0fbd1ba2351
出典データセット
uspto-grants-2003_08
特許番号
US06610692B1

関連ノート

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