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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1886042Generated: November 3, 2026

Methyl iodide → 1H-benzimidazole, 1-methyl-2-(methylsulfonyl)-

https://huagongshe.com/reaction/1886042

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethyl iodideHCID 6328—
ReactantSodium hydrideHCID 24758—
Reactant2-(methylsulfonyl)-1H-benzimidazoleHCID 303526—
SolventDimethylformamideHCID 6228—
Product1H-benzimidazole, 1-methyl-2-(methylsulfonyl)-HCID 64071588.9%

Reaction Conditions

Temperature0 °C

Reaction Steps

To a cooled (0° C.), stirred solution of 2-(methylsulfonyl)-1H-benzimidazole (4.60 g, 0.023 mol) in DMF (25 mL) was added NaH (60% dispersion in mineral oil; 0.94 g, 0.023 mol) in several portions. After 1 hour, iodomethane (3.33 g, 0.023 mol) was added. The cooling bath was removed and stirring was continued for 18 hours. The mixture was recooled to 0° C., H2O (75 mL) was added, and the off-white precipitate was collected by filtration to give 4.30 g (88%) of product m.p. 131°-132° C.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05149700
Source datasetuspto-grants-1992_09
ORD IDord-0331452ae5cb4b1683b71b525695cc46
Source noteuspto-grants-1992_09