Methyl iodide → 2-(Methylsulfanyl)quinazolin-4(1H)-one
Reaction equation
[SH:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[OH-].[Na+].[CH3:15]I>O>[CH3:15][S:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
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.
Workup
- filtrationThe precipitate was collected by filtration
- washwashed with water (3×20 mL)
- customdried in vacuum desiccator over silica gel for 24 h
Sources & evidence
- ORD record
- ord-dc05f9dda02746159671adca50b799ee
- Source dataset
- uspto-grants-1999_08
- Patent number
- US05932584
Reaction notes
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