Ethanethiol → 2-(Ethylthio)quinazolin-7-ol

Participants

Reaction Conditions

Reaction Steps

To a solution of ethanthiol (30 ml) in DCM (50 ml) was added AlCl3 (6 eq). The reaction mixture was cooled to 0° C. and stirred for 10 min under N2 atmosphere. A solution of 2-chloro-7-methoxyquinazoline (1 eq) in DCM (20 ml) was added dropwise to it. The reaction mixture was warmed to room temperature and stirred for 2 h. The solvent was evaporated and residue was partitioned between EtOAc and satd. NaHCO3. The insoluble material was filtered, washed and dried to provide title product as a yellow solid (yield, 60%). The ethyl acetate layer was separated from basic layer, washed with brine and dried over sodium sulfate. Filtration, evaporation and drying under vacuum provide additional amount of product. (yield, 38%). ES/MS m/z 207.0 (MH+).

Provenance & Evidence