Ethyl Acetate → HCID 18681095, compound

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence