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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 321968Generated: October 28, 2026

Dimethylformamide → 2-Benzyl-1-(2-chlorobenzyl)-5-ethoxycarbonylbenzimidazole

https://huagongshe.com/reaction/321968

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
Reactantalpha-Bromo-o-chlorotolueneHCID 11905—
ReactantSodium BicarbonateHCID 516892—
Reactant2-Benzyl-5-ethoxycarbonylbenzimidazoleHCID 10221333—
SolventWaterHCID 962—
SolventEthyl AcetateHCID 8857—
Product2-Benzyl-1-(2-chlorobenzyl)-5-ethoxycarbonylbenzimidazoleHCID 1868115018.7%

Reaction Conditions

Temperature60 °C

Reaction Steps

N,N-dimethylformamide (15 ml), 2-chlorobenzyl bromide (3.94 g) and sodium bicarbonate (1.23 g) are added to 2-benzyl-5-ethoxycarbonyl-benzimidazole (2.37 g) (example 11) and the solution is heated for one hour at 60° C. After adding ethyl acetate (70 ml) and water (70 ml) and separating the solution, 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, a mixture of 2-benzyl-1-(2-chlorobenzyl)-6-ethoxycarbonylbenzimidazole (1.06 g) and 2-benzyl-1-(2-chlorobenzyl)-5-ethoxycarbonylbenzimidazole (0.640 g) is obtained. Separation and purification is performed using medium pressure silica gel column chromatography (eluate: hexane/ethyl acetate=1/4˜0/100) produces medium pressure silica gel column chromatography (eluate: hexane/ethyl acetate=1/4˜0/100).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06211177B1
Source datasetuspto-grants-2001_04
ORD IDord-7a81855d613543aab227f0fe72a70ed0
Source noteuspto-grants-2001_04