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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 636502Generated: October 31, 2026

Water → 4-benzyloxy-1-methyl-2-dimethylamino-1H-benzimidazole

https://huagongshe.com/reaction/636502

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantMethyl iodideHCID 6328—
ReactantSodium hydrideHCID 24758—
Reactant4-benzyloxy-1-methyl-2-methylamino-1H-benzimidazoleHCID 10659480—
SolventDimethylformamideHCID 6228—
Product4-benzyloxy-1-methyl-2-dimethylamino-1H-benzimidazoleHCID 1068422947.5%

Reaction Steps

To a solution of 4-benzyloxy-1-methyl-2-methylamino-1H-benzimidazole (200 mg) in dimethylformamide (2 ml) was added sodium hydride (32.9 mg) under ice-cooling, and the mixture was stirred for 15 minutes. To the mixture was added methyl iodide (127 mg), and the mixture was stirred for 15 minutes under ice-cooling and then for 2 hours at ambient temperature. Water was added to the reaction mixture, and extracted with chloroform. The organic layer was dried over magnesium sulfate and evaporated in vacuo. The residue was purified by flash chromatography (chloroform:methanol=50:1, v/v) to give 4-benzyloxy-1-methyl-2-dimethylamino-1H-benzimidazole (100 mg).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06194396B1
Source datasetuspto-grants-2001_02
ORD IDord-cd427960f30f46b4a0720bcacabe6ebe
Source noteuspto-grants-2001_02