Methyl iodide → 6-Methyl-3-methylsulfanyl-4H-[1,2,4]triazin-5-one

Temperature

40 °C

To a solution of 6-methyl-3-thioxo-3,4-dihydro-1,2,4-triazin-5(2H)-one (4, 5.80 g, 40.6 mmol) in absolute ethanol (250 mL) was added NaOH (1.96 g, 49.1 mmol) followed by MeI (11.5 g, 81.2 mmol). The mixture was heated at 40° C. for 15 h. Most of the solvent was evaporated under reduced pressure. Water was added to the residue. The precipitated white solid was collected by filtration and washed with ethanol to give 5 (3.06 g). The aqueous phase was extracted with CH2Cl2 (80 mL×4). The combined extracts were dried over Na2SO4 and concentrated to give 3.34 g crude product. This was purified by column chromatography on silica gel, and eluted with 1:1 to 1:2 petroleum ether-ethyl acetate to provide 6-methyl-3-(methylthio)-1,2,4-triazin-5(4H)-one (5). MS: m/z, 158 (100%, M+1).

1. customMost of the solvent was evaporated under reduced pressure
2. additionWater was added to the residue
3. filtrationThe precipitated white solid was collected by filtration
4. washwashed with ethanol

ORD record

ord-e9685abb175e4bc2a64e459b47b90f81

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08648073B2