Methyl iodide → 2-(Methylsulfanyl)quinazolin-4(1H)-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-mercaptoquinazolin-4(3H)-one (4.45 g, 25 mmol) and NaOH (1.1 g, 27.5 mmol) in water (125 mL) was added methyl iodide (1.72 mL, 27.5 mmol) and the mixture was stirred at 25° C. for 3 h. The precipitate was collected by filtration, washed with water (3×20 mL) and dried in vacuum desiccator over silica gel for 24 h to give 3.66 g (73%) of the title compound as colorless solid: mp 224-225° C. An analytical sample was recrystallized from methanol-water: mp 225° C.; 1H NMR (CDCl3) δ 11.25 (br s, 1H, NH), 8.27 (dd, 1H, J=1.25, 6.3 Hz, ArH), 7.62 (d, 1H, J=7.3 Hz), 7.44-7.38 (m, 1H, ArH), 2.70 (s, 3H, SCH3); 13C NMR (CDCl3) δ 163.73, 155.76, 149.77, 135.50, 127.30, 126.96, 126.40, 120.37, 13.97.

Provenance & Evidence