Thionyl Chloride → 4-Chloroquinazoline-6-carbonitrile
Reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12](=O)[NH2:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.S(Cl)([Cl:17])=O>P(Cl)(Cl)(Cl)=O>[Cl:17][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]#[N:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture comprising 2 g of 4-hydroxy-6-carbamoylquinazoline, 30 ml of thionyl chloride and 60 ml of phosphorus oxychloride was heated under reflux for 20 hours. The reaction mixture was concentrated under a reduced pressure and the obtained residue was dissolved in 100 ml of ethyl acetate. The obtained solution was washed with water (150 ml), dried over magnesium sulfate and concentrated under a reduced pressure. The obtained residue was introduced into a silica gel column, followed by eluting with ethyl acetate and acetone to give 800 mg of the title compound.