Methyl iodide → HCID 14880637, compound

Participants

Reaction Steps

4.2 g (0.018 mol) of 4-amino-3-methylthio-6-(pent-3-yl)-1,2,4-triazin-5(4H)-one are introduced at room temperature into a mixture of 7.5 ml of 45% strength sodium hydroxide solution and 7.5 ml of toluene. 7.1 g (0.05 mol) of methyl iodide and 0.6 g of tetrabutylammonium bromide are then added all at once at room temperature. The mixture is stirred vigorously, and the temperature rises from 21° C. to 31° C. Stirring of the reaction mixture is continued for 1 hour, and the organic top phase is then removed in a separation funnel and stirred in 100 ml of water. The mixture is extracted with methylene chloride (three times, using 70 ml each time) and then filtered over silica gel, which, after concentrating, gives 3.8 g (87% of theory) of 4-methylamino-3-methylthio-6-(pent-3-yl)-1,2,4-triazin-5-(4H}-one as a colorless oil of refractive index nD20 =1.553.

Provenance & Evidence