Thionyl Chloride → 4-Chloro-6-methoxy-7-(2-morpholinoethoxy)quinazoline

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Reaction Steps

A mixture of 6-methoxy-7-(2-morpholinoethoxy)-3,4-dihydroquinazolin-4-one (310 mg, 1.02 mmol), thionyl chloride (10 ml) and DMF (2 drops) was heated at reflux for 4 hours and allowed to cool. Excess thionyl chloride was removed by evaporation and the residue was azeotroped with toluene. The residue was partitioned between aqueous sodium hydrogen carbonate and methylene chloride. The organic layer was separated, washed with brine and filtered through phase separating paper. The volatiles were removed by evaporation and the residue purified by column chromatography eluting with methylene chloridelinethanol (96/4) to give 4-chloro-6-methoxy-7-(2-morpholinoethoxy)quinazoline (225 mg, 68%).

Provenance & Evidence