Dimethylformamide → 7-(Benzyloxy)-4-chloroquinazoline

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Reaction Steps

A mixture of 7-benzyloxy-3,4-dihydroquinazolin-4-one (11 g, 43.6 mmol) and DMF (1 ml) in thionyl chloride (100 ml) was heated at reflux for 1.5 hours. Excess thionyl chloride was removed by evaporation and the residue azeotroped with toluene. The residue was partitioned between methylene chloride and water and saturated aqueous sodium hydrogen carbonate was added until the aqueous layer was at about pH9. The organic layer was separated, washed with water, brine, dried (MgSO4) and evaporated to give 7-benzyloxy-4-chloroquinazoline (10.5 g, 89%).

Provenance & Evidence