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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1594521Generated: November 1, 2026

Methyl iodide → Methyl 4-[(5,6-dichloro-2-{[4-(methoxy)-phenyl]imino}-3-methyl-2,3-dihydro-1h-benzimidazol-1-yl)methyl]benzoate

https://huagongshe.com/reaction/1594521

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethyl iodideHCID 6328—
ReactantDichloromethaneHCID 6344—
ReactantSodium hydrideHCID 24758—
ReactantMethyl 4-[(5,6-dichloro-2-{[4-(methoxy)-phenyl]amino}-1h-benzimidazol-1-yl)methyl]benzoateHCID 69417835—
SolventDimethylformamideHCID 6228—
SolventEthyl AcetateHCID 8857—
ProductMethyl 4-[(5,6-dichloro-2-{[4-(methoxy)-phenyl]imino}-3-methyl-2,3-dihydro-1h-benzimidazol-1-yl)methyl]benzoateHCID 69418089—

Reaction Steps

To a solution of the title compound of Example 19, Step B (0.45 mmol, 203 mg) in DMF (3 mL) was added NaH (0.54 mmol, 21 mg of 60% suspension in mineral oil). After 10 min MeI (0.9 mmol, 56 μL) was added and the reaction was allowed to stand at ambient temperature for 2 h. Aqueous workup with CH2Cl2/saturated NaHCO3, followed by flash chromatography on silica eluting with 30% and 40% EtOAc in hexanes, afforded the product as a white solid. LC-MS (ESI, Method B): 1.93 min. m/z 470.2 (M+1).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07301036B2
Source datasetuspto-grants-2007_11
ORD IDord-54602a73e44a40199a32c2e4e6427d98
Source noteuspto-grants-2007_11