Pyridine → N-(5-bromo-2-pyridinyl)-S,S-dimethylsulfilimine

Temperature

-10 °C

A mixture containing about 17 mmol of N-5-bromo-2-pyridinyl-S,S-dimethylsulfilimine in about 30 mL of dichloromethane solution prepared as in Example 3A omitting the recovery step was diluted with 43 mL of dichloromethane and then 10.0 g (58 mmol) of 2-amino-5-bromopyridine, 5.5 g (70 mmol) of pyridine, and 14.2 g (74 mmol) of 4-methylbenzenesulfonyl chloride were added sequentially with stirring and cooling at -10° C. The mixture was allowed to warm to 20° C. with stirring. A white precipitate formed quickly. An additional 1.6 g (20 mmol) of pyridine was added and the mixture was allowed to stand for 3 days. Dichloromethane (25 mL) was added to dissolve all the solids and the resulting solution was washed with 150 mL of 0.1N aqueous hydrochloric acid. The aqueous layer was back-extracted with dichloromethane and the combined organic phases were dried over magnesium sulfate and concentrated by evaporation under reduced pressure. The yellow solid residue was recrystallized from 175 mL of acetonitrile and the resulting yellow solid (a first crop of 8.3 g and a second crop of 1.5 g) was recovered to obtain the title compound (41 percent of theory).

1. additionA mixture containing
2. temperatureto warm to 20° C.
3. stirringwith stirring
4. customA white precipitate formed quickly
5. dissolutionto dissolve all the solids
6. washthe resulting solution was washed with 150 mL of 0.1N aqueous hydrochloric acid
7. extractionThe aqueous layer was back-extracted with dichloromethane
8. dry with materialthe combined organic phases were dried over magnesium sulfate
9. concentrationconcentrated by evaporation under reduced pressure
10. customThe yellow solid residue was recrystallized from 175 mL of acetonitrile
11. customthe resulting yellow solid (a first crop of 8.3 g and a second crop of 1.5 g) was recovered

ORD record

ord-9cefa39aba85434580d11a2472b78252

Source dataset

uspto-grants-2000_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06114580