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

HRID 1699613ノート

反応式

HRID 1699613 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 867577922-Benzyl-5-ethoxy-carbonylbenzimidazole

試薬・触媒・溶媒 1

HCID 23925Iron触媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ea9a9c3c3b7c41199bf454ff5c2f2e6a
出典データセット
uspto-grants-2002_02
特許番号
US06348032B1

反応ノート

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