Thionyl Chloride → 7-Benzyloxy4-chloroquinazoline hydrochloride

Participants

Reaction Steps

A mixture of 7-benzyloxy-3,4-dihydroquinazolin-4-one (800 mg, 3.177 mmol) and DMF (100 μl) in thionyl chloride (20 ml, 0.27 mmol) was heated at reflux for 3 hours. Excess thionyl chloride was removed by evaporation and the residue azeotroped with toluene and dried under vacuum to give 7-benzyloxy-4-chloroquinazoline hydrochloride (835 mg, 86%) as a cream solid. m.p. 131-132° C. 1H NMR Spectrum: (DMSOd6; CF3COOD) 5.32(s, 2H); 7.29(d, 1H); 7.34-7.52(m, 6H); 8.12(d, 1H); 9.03(s, 1H) MS-ESI: 270 [MH]+

Provenance & Evidence