Methyl iodide → HCID 14031860, compound

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:20]=[C:19]3[N:10]([C:11](=[O:21])[NH:12][C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=43)[N:9]=2)=[CH:4][CH:3]=1.[CH3:22][O-].[Na+].CI>CS(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:20]=[C:19]3[N:10]([C:11](=[O:21])[N:12]([CH3:22])[C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=43)[N:9]=2)=[CH:6][CH:7]=1

Participants

Procedure

To a mixture of 2-(4-chlorophenyl)-[1,2,4]triazolo[1,5-c]quinazolin-5(6H)one (6 g) in dry dimethylsulphoxide (150 ml) is added sodium methoxide (1.3 g). The mixture is heated under nitrogen for one hour at 85° and methyl iodide (1.3 ml) in dimethyl sulphoxide (10 ml) added. A white solid forms rapidly. The reaction mixture is heated three hours longer, cooled and poured into ice water (800 ml). The precipitated white solid is washed with water, air dried (7.2 g) and recrystallized from dimethylacetamide twice to afford pure 2-(4-chlorophenyl)6-methyl-[1,2,4]triazolo[1,5-c]quinazolin-5(6H)one, mp 323°-325°.