Ethanol → HCID 15185606, compound

HRID 1699609Notes

Reaction equation

HRID 1699609 reaction equation
[CH2:1]([OH:3])[CH3:2].[C:4]([NH:7][C:8]1[C:9](CC)=[C:10]([CH:14]=[CH:15][C:16]=1[N+:17]([O-])=O)[C:11]([O-])=[O:12])(=O)[CH3:5]>C(O)(=O)C>[CH2:1]([O:3][C:11]([C:10]1[CH:14]=[CH:15][C:16]2[N:17]=[C:4]([CH3:5])[NH:7][C:8]=2[CH:9]=1)=[O:12])[CH3:2]

Participants

4

Reactant 2

HCID 702EthanolHCID 18680885HCID 18680885, compound

Product 1

HCID 15185606HCID 15185606, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Reduced iron (6.64 g), ethanol (48 ml) and acetic acid (24 ml) are added to 3-acetylamino-4-nitro-ethylbenzoate (3.00 g), and the solution is refluxed by heating for 12 hours. Solid materials are removed using filter aid, and the filtrate is concentrated under reduced pressure. Ethanol (100 ml) and 35% hydrochloric acid (5.2 g) are added to the residue and the solution is refluxed by heating for five hours. The reaction solution is neutralized with sodium bicarbonate (6.3 g). The filtrate obtained through filtration is concentrated under reduced pressure. Ethyl acetate (70 ml) and water (70 ml) are added to the obtained residue, and the solution is separated. The organic layer is washed with water three times and extraction is performed on the aqueous layer using ethyl acetate three times. By concentrating the obtained organic layer under reduced pressure, 5-ethoxycarbonyl-2-methylbenzimidazole (1.53 g ) powder is obtained. 1H-NMR (CDCl3, δ): 1.41 (3H, t, J=6.9 Hz), 2.67 (3H, s), 4.40 (2H, q, J=7.1 Hz), 7.55 (1H, d, J=8.4 Hz), 7.96 (1H, dd, J=8.4 and 1.5 Hz), 8.27 (1H, d, J=1.4 Hz).

Workup

  1. temperaturethe solution is refluxed
  2. temperatureby heating for 12 hours
  3. customSolid materials are removed
  4. filtrationusing filter aid
  5. concentrationthe filtrate is concentrated under reduced pressure
  6. additionEthanol (100 ml) and 35% hydrochloric acid (5.2 g) are added to the residue
  7. temperaturethe solution is refluxed
  8. temperatureby heating for five hours
  9. customThe filtrate obtained through filtration
  10. concentrationis concentrated under reduced pressure
  11. additionEthyl acetate (70 ml) and water (70 ml) are added to the obtained residue
  12. customthe solution is separated
  13. washThe organic layer is washed with water three times and extraction
  14. concentrationBy concentrating the obtained organic layer under reduced pressure

Sources & evidence

ORD record
ord-121a7c6140034a36b1212a5aec32c6ed
Source dataset
uspto-grants-2002_02
Patent number
US06348032B1

Reaction notes

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