Ethanol → 2-Benzyl-5-ethoxycarbonylbenzimidazole

HRID 321964ノート

反応式

HRID 321964 の反応式
[N+:1]([C:4]1[C:5](CC)=[C:6]([CH:10]=[CH:11][C:12]=1[NH:13][C:14](=O)[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:7]([O-:9])=[O:8])([O-])=O.[CH2:25](O)[CH3:26]>C(O)(=O)C>[CH2:15]([C:14]1[NH:1][C:4]2[CH:5]=[C:6]([C:7]([O:9][CH2:25][CH3:26])=[O:8])[CH:10]=[CH:11][C:12]=2[N:13]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

参加物

4

反応物 2

HCID 702EthanolHCID 701409133-Nitro-4-phenylacetylamino-ethylbenzoate

生成物 1

HCID 102213332-Benzyl-5-ethoxycarbonylbenzimidazole

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A mixture of 3-nitro-4-phenylacetylamino-ethylbenzoate (3.60 g), ethanol (47 ml), acetic acid (23 ml) and reduced iron (6.4 g) is refluxed for four hours. Solids are separated through filtration and the filtrate is concentrated. Ethanol (50 ml) and 35% hydrochloric acid (5 g) are added to the residue and the solution is refluxed for 40 hours. The solution is neutralized with sodium bicarbonate and chloroform extraction is performed. The organic layer is concentrated under reduced pressure and then purified using silica gel column chromatography. Thus, 2-benzyl-5-ethoxycarbonylbenzimidazole (2.30 g) is obtained. 1H-NMR (CDCl3, δ): 1.39 (3H, t, J=7.1 Hz), 4.26 (2H, s), 4.37 (2H, q, J=7.1 Hz), 7.22-7.36 (5H, m), 7.50 (1H, d, J=8.6 Hz), 7.94 (1H, dd, J=1.5 and 8.6 Hz), 8.23 (1H, d, J=1.3 Hz).

後処理

  1. temperatureis refluxed for four hours
  2. customSolids are separated through filtration
  3. concentrationthe filtrate is concentrated
  4. additionEthanol (50 ml) and 35% hydrochloric acid (5 g) are added to the residue
  5. temperaturethe solution is refluxed for 40 hours
  6. extractionThe solution is neutralized with sodium bicarbonate and chloroform extraction
  7. concentrationThe organic layer is concentrated under reduced pressure
  8. custompurified

出典と根拠

ORDレコード
ord-272485b9e0474238a166b526b3f48b61
出典データセット
uspto-grants-2001_04
特許番号
US06211177B1

反応ノート

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