Water → S-(6-Chloro-3-pyridyl) O-Ethyl Dithiocarbonate

Temperature

60 °C

In 1N hydrochloric acid (10 ml) was dissolved 5-amino-2-chloropyridine (643 mg, 3.00 mmol). A water (1 ml) solution of sodium nitrite (207 mg, 3.00 mmol) was added dropwise to the resulting solution at −5° C. After the reaction mixture was stirred at 60° C. for 30 minutes, a water (1 ml) solution of potassium O-ethyl dithiocarbonate (481 mg, 3.00 mmol) was added dropwise thereto at the same temperature. The reaction mixture was then stirred at 80° C. for 1 hour, followed by cooling to room temperature. Ethyl acetate was added, and the resulting mixture was washed with a saturated aqueous solution of sodium bicarbonate. The organic layer was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was subjected to flash chromatography on a silica gel column, and the fraction obtained from the hexane:ethyl acetate=49:1 eluate was concentrated under reduced pressure, whereby the title compound (148 mg, 0.63 mmol, 21%) was obtained as a yellow oil.

1. stirringThe reaction mixture was then stirred at 80° C. for 1 hour
2. temperatureby cooling to room temperature
3. washthe resulting mixture was washed with a saturated aqueous solution of sodium bicarbonate
4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
5. filtrationAfter filtration
6. concentrationthe filtrate was concentrated under reduced pressure
7. customthe fraction obtained from the hexane

ORD record

ord-5ff93825b7014bc6950e10bc985fd36f

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07399775B2