Hydrochloric Acid → 4-Fluoro-3-((trifluoromethyl)sulfonyl)benzenesulfonamide

Temperature

-50 °C

The solution from EXAMPLE 14 was charged into a flask fitted with overhead stirrer, nitrogen inlet, temperature probe and cooling bath. The solution was cooled down to −50° C. using an acetone/dry ice bath. Ammonium hydroxide (238 g) solution was slowly added to the reaction mixture through an additional funnel. The internal temperature was kept at about −40° C. HPLC showed the reaction was completed. The solution was cooled down to −60° C. 6 N HCl (600 g) was added to the reaction mixture slowly to keep the temperature under −35° C. The mixture was warmed up to room temperature. The layers were separated, and the organic layer was washed twice with 375 g of 4 N HCl. The organic layer was distilled down under vacuum with bath temperature from 40 to 50° C. Toluene (700 g) was added to the residue, and the mixture was stirred at room temperature for an hour. The mixture was filtered and washed with toluene to obtain the title compound.

1. customfitted with overhead stirrer, nitrogen inlet
2. temperaturetemperature probe and cooling bath
3. customwas kept at about −40° C
4. temperatureThe solution was cooled down to −60° C
5. customunder −35° C
6. temperatureThe mixture was warmed up to room temperature
7. customThe layers were separated
8. washthe organic layer was washed twice with 375 g of 4 N HCl
9. distillationThe organic layer was distilled down under vacuum with bath temperature from 40 to 50° C
10. additionToluene (700 g) was added to the residue
11. filtrationThe mixture was filtered
12. washwashed with toluene

ORD record

ord-b0fbaf2a8a1a4e778a4ca64d41507e34

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08168784B2