4-Toluenesulfonyl chloride → HCID 67118558, compound

Temperature

-20 °C

4-Oxothiane (2.32 g, 20.0 mmol) was dissolved in ethanol. To the solution were added hydroxylamine hydrochloride (2.78 g, 40.0 mmol) and potassium carbonate (5.52 g, 40.0 mmol), and the mixture was heated to reflux for 1 hour. Water and ethyl acetate were added to the mixture, and the mixture was extracted. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was then evaporated under reduced pressure. The resulting residue was dissolved in pyridine (20 mL). p-Toluenesulfonyl chloride (6.46 g, 24.0 mmol) was added at −20° C., and the mixture was stirred at −20° C. for 1 hour. Water and ethyl acetate were added to the mixture, and the mixture was extracted. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was then evaporated under reduced pressure. The resulting residue was dissolved in ethanol, and an ethanol solution of potassium ethoxide (4 mol/L; 15.7 mL, 40.0 mmol) was added to the solution at 0° C., then the mixture was stirred for 1 hour. After stirring the mixture at 50° C. for another 1 hour, water and ethyl acetate were added thereto, and the mixture was extracted. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was then evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate) to give 3-amino-4,4-diethoxythiopyran (2.31 g, 56%).

1. temperaturethe mixture was heated
2. temperatureto reflux for 1 hour
3. extractionthe mixture was extracted
4. washThe organic layer was washed with brine
5. dry with materialdried over anhydrous magnesium sulfate
6. customThe solvent was then evaporated under reduced pressure
7. dissolutionThe resulting residue was dissolved in pyridine (20 mL)
8. extractionthe mixture was extracted
9. washThe organic layer was washed with brine
10. dry with materialdried over anhydrous magnesium sulfate
11. customThe solvent was then evaporated under reduced pressure
12. dissolutionThe resulting residue was dissolved in ethanol
13. stirringthe mixture was stirred for 1 hour
14. stirringAfter stirring the mixture at 50° C. for another 1 hour
15. extractionthe mixture was extracted
16. washThe organic layer was washed with brine
17. dry with materialdried over anhydrous magnesium sulfate
18. customThe solvent was then evaporated under reduced pressure
19. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate)

ORD record

ord-41afe41ade6a4a4cb37feba815c132e5

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07928098B2