Imidazole → 1-(6-Chloro-3,4-dihydronaphthalen-1-yl)-1H-imidazole

Participants

Reaction Steps

0.218 ml of thionyl chloride is added within a period of 15 minutes to a solution of 815 mg of imidazole in 3.2 ml of methylene chloride. At the end of the exothermic reaction, 451 mg of 6-chloro-1-tetralone are added to the resulting suspension. After stirring for 20 hours at room temperature, 497 mg of potassium carbonate in 2 ml of water are added, and the mixture is extracted twice with chloroform. After drying the organic extracts over sodium sulfate, concentration is carried out under reduced pressure. The resulting crude product is purified by column chromatography (SiO2, 0.04-0.063 mesh, 0.15 bar, ethyl acetate); m.p. (after dry crystallisation from ether) 68°-72°.

Provenance & Evidence