Ethyl Acetate → HCID 18681095, compound

HRID 1699639Notes

Reaction equation

HRID 1699639 reaction equation
[C:1]([NH:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([O-:12])=[O:11])=[C:8](CC)[C:7]=1[NH2:17])(=O)[CH2:2][CH3:3].C(=O)([O-])[O-].[K+].[K+].[F:24][C:25]1[CH:40]=[CH:39][C:28]([CH2:29][O:30][C:31]2[CH:38]=[CH:37][C:34]([CH2:35]Br)=[CH:33][CH:32]=2)=[CH:27][CH:26]=1.[C:41](OCC)(=O)[CH3:42]>O>[CH2:41]([O:12][C:10]([C:9]1[CH:13]=[CH:14][C:6]2[N:5]=[C:1]([CH2:2][CH3:3])[N:17]([CH2:35][C:34]3[CH:37]=[CH:38][C:31]([O:30][CH2:29][C:28]4[CH:39]=[CH:40][C:25]([F:24])=[CH:26][CH:27]=4)=[CH:32][CH:33]=3)[C:7]=2[CH:8]=1)=[O:11])[CH3:42]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 18680960HCID 18680960, compoundHCID 18680963HCID 18680963, compound

Product 1

HCID 18681095HCID 18681095, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 4-propionylamino-3-amino-ethylbenzoate (0.534 g), potassium carbonate (0.374 g), 4-(4-fluorobenzyloxy)benzyl bromide (0.800 g), ethyl acetate (5 ml) and water (3 ml) is stirred for 16 hours at 75° C. The organic layer is concentrated, and ethanol and 36% hydrochloric acid (0.46 g) are added to the obtained residue. The residue is stirred for two hours as it is refluxed by heating. After neutralizing it by adding potassium carbonate, the solvent is concentrated under reduced pressure. Ethyl acetate and water are added and extraction is performed. The organic layer is concentrated under reduced pressure, purified using silica gel column chromatography (eluate: hexane/ethyl acetate=1/1), and thus, 6-ethoxycarbonyl-2-ethyl-1-[4-(4-fluorobenzyloxy)benzyl]benzimidazole (0.228 g) is obtained. 1H-NMR (CDCl3δ): 1.40 (3H, t, J=7.1 Hz), 1.42 (3H, t, J=7.5 Hz), 2.86 (2H, q, J=7.5 Hz), 4.38 (2H, q, J=7.1 Hz), 4.97 (2H, s), 5.32 (2H, s), 6.88 (2H, q, J=8.7 Hz), 6.98 (2H, d, J=8.7 Hz), 7.05 (2H, t, J=8.7 Hz), 7.37 (2H, m), 7.76 (2H, d, J=8.4 Hz), 7.98 (1H, dd, J=1.5 and 8.5 Hz), 8.02 (1H, s).

Workup

  1. concentrationThe organic layer is concentrated
  2. additionethanol and 36% hydrochloric acid (0.46 g) are added to the obtained residue
  3. stirringThe residue is stirred for two hours as it
  4. temperatureis refluxed
  5. temperatureby heating
  6. additionby adding potassium carbonate
  7. concentrationthe solvent is concentrated under reduced pressure
  8. additionEthyl acetate and water are added
  9. extractionextraction
  10. concentrationThe organic layer is concentrated under reduced pressure
  11. custompurified

Sources & evidence

ORD record
ord-8995e3a0deb14bffae0ac4997e9de0d3
Source dataset
uspto-grants-2002_02
Patent number
US06348032B1

Reaction notes

Loading…