Ethanol → 2-Benzyl-5-ethoxycarbonylbenzimidazole

HRID 321964노트

반응식

HRID 321964 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

HCID 102213332-Benzyl-5-ethoxycarbonylbenzimidazole

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-272485b9e0474238a166b526b3f48b61
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211177B1

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