Hydrochloric Acid → N-Allylheptadecafluorooctanesulphonamide

Temperature

25 °C

Allyl amine (45.0 milliliters, 3.0 molar equivalent) and isopropyl ether (200.0 milliliters) were charged into a 3-neck 500-milliliter round bottom flask equipped with a Claisen joint adapter, dropping funnel and overhead mechanical stirrer at room temperature under a nitrogen blanket. The Claisen joint adapter was attached to a Thermowatch® thermometer adapter and water cooled condenser (to the nitrogen inlet). The mixture was warmed to 25° C. with stirring. Perfluoro-1-octanesulfonyl fluoride (100.0 grams, 1.0 molar equivalent, Aldrich Chemical Co.) was added by the dropping funnel over 1.5 hours. The reaction mixture was maintained at about 25° C. by immersing the reaction flask in a room temperature water bath. After the addition was completed, the reaction mixture was heated for 2 hours at 30° C., followed by 2 hours at 40° C. Upon cooling to 30° C. using a water bath, 120 milliliters of a 9% aqueous hydrochloric acid solution was added over 15 minutes while maintaining the temperature at 25° C. After separation of the layers in a separatory funnel, the organic layer was washed with an aqueous 4.5% hydrochloric acid 4.0% ferrous sulfate solution. The organic phase was isolated and evaporated in vacuo, further dried under vacuum (0.1 millimeters Hg) in a water bath at 70° C. for 0.5 hours to give a red pasty solid. The crude reaction product was subjected to high vacuum distillation to give a slightly yellow solid (boiling point 98° C.) (0.1 millimeters Hg)(85.62 grams, 80% purified yield).

1. customequipped with a Claisen joint adapter
2. customat room temperature
3. temperatureThe reaction mixture was maintained at about 25° C.
4. customin a room temperature
5. additionAfter the addition
6. temperaturethe reaction mixture was heated for 2 hours at 30° C.
7. temperatureUpon cooling to 30° C.
8. temperaturewhile maintaining the temperature at 25° C
9. customAfter separation of the layers in a separatory funnel
10. washthe organic layer was washed with an aqueous 4.5% hydrochloric acid 4.0% ferrous sulfate solution
11. customThe organic phase was isolated
12. customevaporated in vacuo
13. customfurther dried under vacuum (0.1 millimeters Hg) in a water bath at 70° C. for 0.5 hours
14. customto give a red pasty solid
15. customThe crude reaction product
16. distillationwas subjected to high vacuum distillation

ORD record

ord-f31afdde51954d3897ab827c65dadbc8

Source dataset

uspto-grants-1994_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05348769