反应详情

温度

-45 °C

To a solution of 2-methyl-N-{(1E)-[6-(trifluoromethyl)-3-pyridinyl]methylene}-2-propanesulfinamide (76.8 g, 276 mmol) in dichloromethane (920 mL) at −45° C. was added methylmagnesium bromide (3.0 M in THF; 184 mL, 552 mmol). The mixture was stirred at −45° C. for 4 h. The reaction mixture was warmed to −20° C. Additional methylmagnesium bromide (3.0 M in THF; 276 mL, 828 mmol) was added at −20° C. The reaction mixture was warmed to 0° C. and was quenched with saturated aqueous ammonium chloride (300 mL). The mixture was allowed to warm to ambient temperature. The organic layer was separated and the aqueous layer was extracted with dichloromethane (3×). The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated. The concentrate was recrystallized using ethyl alcohol (500 mL). Then white solid was filtered and dried under reduced pressure (41.6 g). MS 295.0 (M+1).

1. temperatureThe reaction mixture was warmed to −20° C
2. temperatureThe reaction mixture was warmed to 0° C.
3. customwas quenched with saturated aqueous ammonium chloride (300 mL)
4. temperatureto warm to ambient temperature
5. customThe organic layer was separated
6. extractionthe aqueous layer was extracted with dichloromethane (3×)
7. washThe combined organic extracts were washed with brine
8. dry with materialdried over magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated
11. customThe concentrate was recrystallized
12. filtrationThen white solid was filtered
13. customdried under reduced pressure (41.6 g)