Methanesulfonyl chloride → HCID 67299734, compound

Temperature

92.5 °C

Mixture of 4-Methanesulfonyl-2,3-dimethyl-pyridine 1-oxide (100 g) and methane sulfonyl chloride (300 ml) was heated to 90-95° C. and maintained at the same temperature for 3-4 hrs. 20% sodium hydroxide solution (1500 ml) was cooled to 0-5° C. separately and the above reaction mixture was added to this solution slowly for a period of 2-3 hrs and maintained at the same temperature for 1-2 hrs. The solid was filtered and washed with DM water (200 ml). DM water (400 ml) was added to the wet material and stirred for 30-60 min at 25-35° C. The solid was filtered and washed with DM water (100 ml). Ethylacetate (600 ml) was added to the wet material followed by heating to get clear solution and adding carbon (10 gm) and stirring the reaction mixture for 30 minutes. The resultant reaction mass was filtered through hiflow bed and washed with ethyl acetate (200 ml). The filtrate was dried with sodium sulfate (100 gm). Subsequently, conc. HCl (60 ml) was added, heated to reflux and maintained at the same temperature for 30-60 min. The reaction mixture was cooled to 25-30° C., then to 0-5° C. and maintained at the same temperature for 1-2 hrs. The solid was then filtered and washed with ethylacetate (100 ml). The wet compound was dried at 50-60° C. 90 g of the title compound was obtained.

1. temperaturemaintained at the same temperature for 3-4 hrs
2. additionthe above reaction mixture was added to this solution slowly for a period of 2-3 hrs
3. temperaturemaintained at the same temperature for 1-2 hrs
4. filtrationThe solid was filtered
5. washwashed with DM water (200 ml)
6. additionDM water (400 ml) was added to the wet material
7. filtrationThe solid was filtered
8. washwashed with DM water (100 ml)
9. additionEthylacetate (600 ml) was added to the wet material
10. temperatureby heating
11. customto get clear solution
12. additionadding carbon (10 gm)
13. stirringstirring the reaction mixture for 30 minutes
14. customThe resultant reaction mass
15. filtrationwas filtered through hiflow bed
16. washwashed with ethyl acetate (200 ml)
17. dry with materialThe filtrate was dried with sodium sulfate (100 gm)
18. additionSubsequently, conc. HCl (60 ml) was added
19. temperatureheated
20. temperatureto reflux
21. temperaturemaintained at the same temperature for 30-60 min
22. temperatureThe reaction mixture was cooled to 25-30° C.
23. temperatureto 0-5° C. and maintained at the same temperature for 1-2 hrs
24. filtrationThe solid was then filtered
25. washwashed with ethylacetate (100 ml)
26. customThe wet compound was dried at 50-60° C

ORD record

ord-7bb774fcc8fc4164a4bc9b7cbc8579fb

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08513427B2