Acetic Acid → 2-Benzyl-5-ethoxy-carbonylbenzimidazole

HRID 1699613노트

반응식

HRID 1699613 반응식
[N+:1]([C:4]1[C:5]([CH2:23]C)=[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([O-])=O)([O-])=O.[CH2:25]([OH:27])[CH3:26].C(O)(=[O:30])C>[Fe]>[CH2:15]([C:14]1[N:1]=[C:4]2[C:5](=[C:23]=[O:30])[C:6]([O:27][CH2:25][CH3:26])=[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

5

반응물 3

HCID 176Acetic AcidHCID 702EthanolHCID 701409133-Nitro-4-phenylacetylamino-ethylbenzoate

생성물 1

HCID 867577922-Benzyl-5-ethoxy-carbonylbenzimidazole

시약·촉매·용매 1

HCID 23925Iron촉매

실험 절차

A mixture of 3-nitro-4-phenylacetylamino-ethylbenzoate (3.60 g), ethanol (47 ml), acetic acid (23 ml) and iron (6.4 g) is refluxed by heating 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 stirred for 40 hours as it is refluxed by heating. 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-ethoxy-carbonylbenzimidazole (2.30 g) is obtained. 1H-NMR (CDCl3, δ): 1.39 (3H, t, J =7.1Hz), 4.26 (2H, s), 4.37 (2H, q, J=7.1Hz), 7.22-7.36 (5H, m), 7.50 (1H, d, J=8.6Hz), 7.94 (1H, dd, J=1.5 and 8.6Hz), 8.23 (1H, d, J=1.3Hz).

후처리

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

출처 및 근거

ORD 기록
ord-ea9a9c3c3b7c41199bf454ff5c2f2e6a
출처 데이터셋
uspto-grants-2002_02
특허 번호
US06348032B1

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