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

Participants

Reaction Steps

A mixture of 6-methoxy-7-(2-methylthioethoxy)-3,4-dihydroquinazolin-4-one (1.07 g, 4.0 mmol), thionyl chloride (20 ml) and DMF (4 drops) was heated at reflux for 2 hours and then allowed to cool. The excess thionyl chloride was removed by evaporation and the residue was azeotroped with toluene. The solid residue was partitioned between aqueous sodium hydrogen carbonate and methylene chloride, the organic phase was separated and washed with brine. The organic phase was passed through phase separating paper, and the solvent removed by evaporation to give 4-chloro-6-methoxy-7-(2-methylthioethoxy)quinazoline (810 mg, 71%).

Provenance & Evidence