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

Participants

Reaction Steps

A mixture of 6-methoxy-7-(2-thiomorpholinoethoxy)-3,4-dihydroquinazolin-4-one (1.5 g, 4.6 mmol), thionyl chloride (25 ml) and DMF (0.2 ml) was heated at reflux for 2 hours. Excess thionyl chloride was removed by evaporation and the residue azeotroped with toluene. The resulting gum was partitioned between aqueous sodium hydrogen carbonate solution and methylene chloride. The organic layer was separated and the aqueous layer extracted with methylene chloride (4×40 ml). The combined extracts were passed through phase separating paper, the solvent removed by evaporation and the residue purified by column chromatography eluting with methylene chloride/methanol (95/5). The purified product was triturated with acetone to give 4-chloro-6-methoxy-7-(2-thiomorpholinoethoxy)quinazoline (400 mg, 25%) as an orange/brown solid.

Provenance & Evidence