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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 518031Generated: October 26, 2026

N,N-Diethylaniline → 2-Chloro-5-fluoro-1-methyl-1H-benzimidazole

https://huagongshe.com/reaction/518031

Reaction equation

Participants

RoleNameHCIDCharge
ReactantN,N-DiethylanilineHCID 7061—
ReactantPhosphorus oxychlorideHCID 24813—
Reactant5-Fluoro-1-methyl-1H-benzo[d]imidazol-2(3H)-oneHCID 22028684—
Product2-Chloro-5-fluoro-1-methyl-1H-benzimidazoleHCID 21985828—

Reaction Steps

3.9 g 5-fluoro-1-methyl-1,3-dihydro-benzimidazol-2-one are suspended in 80 ml phosphorus oxychloride and the reaction mixture is stirred for 2 hours at reflux temperature. 50 ml diethylaniline are added. The reaction mixture is stirred for a further 10 minutes at reflux temperature and slowly combined with ice water. The product is extracted with dichloromethane and purified by chromatography (silica gel, cyclohexane, methylene chloride/acetone 20/1). 1.4 g product are obtained as a solid. M.p=138-141° C.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09115142B2
Source datasetuspto-grants-2015_08
ORD IDord-e3740736cb394932b270b895a29f7e62
Source noteuspto-grants-2015_08