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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 855696Generated: October 28, 2026

Dimethylformamide → 4-Chloro-6-methoxy-7-(2-(imidazol-1-yl)ethoxy)quinazoline

https://huagongshe.com/reaction/855696

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantThionyl ChlorideHCID 24386—
Reactant7-(2-(Imidazol-1-yl)ethoxy)-6-methoxy-3,4-dihydroquinazolin-4-oneHCID 135490844—
SolventTolueneHCID 1140—
Product4-Chloro-6-methoxy-7-(2-(imidazol-1-yl)ethoxy)quinazolineHCID 1114126159%

Reaction Conditions

Temperature0 °C

Reaction Steps

A mixture of 7-(2-(imidazol-1-yl)ethoxy)-6-methoxy-3,4-dihydroquinazolin-4-one (412 mg, 1.44 mmol), thionyl chloride (5 ml) and DMF (0.2 ml) was heated at reflux for 1 hour. The mixture was diluted with toluene and the volatiles were removed by evaporation. The residue was suspended in methylene chloride, cooled to 0° C. and aqueous sodium hydrogen carbonate solution was added. The resulting precipitate was collected by filtration and dried under vacuum to give 4-chloro-7-(2-(imidazol-1-yl)ethoxy)-6-methoxyquinazoline (258 mg, 59%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07262201B1
Source datasetuspto-grants-2007_08
ORD IDord-1c4372829a48412cb9115c3161ac6d47
Source noteuspto-grants-2007_08