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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 969540Generated: October 30, 2026

Carbon Dioxide → 7-Benzyloxy-2-methyl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzimidazole-5-carboxylic Acid Dimethylamide

https://huagongshe.com/reaction/969540

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCarbon DioxideHCID 280—
ReactantDimethylamineHCID 674—
ReactantTriphenylphosphineHCID 11776—
Reactant4-Benzyloxy-6-bromo-2-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzimidazoleHCID 46221162—
Catalystpalladium(II) acetateHCID 167845—
Product7-Benzyloxy-2-methyl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzimidazole-5-carboxylic Acid DimethylamideHCID 4622116365%

Reaction Steps

5.8 g (13 mmol) 4-Benzyloxy-6-bromo-2-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzimidazole, 1.3 g (5.2 mmol) triphenylphosphine, 0.4 g (1.9 mmol) palladium(II) acetate and 80 ml (160 mmol) dimethylamine (2M in THF) were transferred to an autoclave and carbonylated (6 bar CO2) at 120° C. for 16 h. The catalyst was filtered off and the filtrate was concentrated in vacuo. The crystallization of the residue from diisopropyl ether afforded 3.7 g (65%) of the title compound as a white solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07307084B2
Source datasetuspto-grants-2007_12
ORD IDord-4012a087390c4199acd52f25c093bb2d
Source noteuspto-grants-2007_12