Trifluoromethanesulfonamide

Reaction

Trifluoromethanesulfonamide can react with paraformaldehyde in sulfuric acid to give open chain and cyclic condensation products, or in ethyl acetate to give oxy-methylated products.

Chemical Properties

White to off-white solid

Uses

Trifluoromethanesulfonamide is used as an intermediate in synthetic chemistry. It is used in the preparation of specific inhibitors of mammalian secreted phospholipases A2. It is also involved in the synthesis of ecicosanoids.

Application

It is known that benzylamine-type trifluoromethanesulfonamide derivatives such as N-benzyltrifluoromethanesulfonamide and the like and trifluoromethanesulfonamide derivatives having a condensed heterocyclic ring structure have herbicidal activity so that they are used as a herbicide.

Synthesis

15.39 trifluoromethanesulfonyl chloride dissolved in 103 g of anhydrous isopropyl ether is charged to a reactor. The medium is cooled to 5 °C. and the ammonia is added slowly over 2 hours. After 5 hours of stirring at 5° C., 24.8 g of water are added to dissolve the salts. The medium is then acidified by adding 20.7 g of a 36% aqueous hydrochloric acid solution.   
After a further addition of 13 g of water, the phases are separated. The aqueous phase is washed with 50 g of isopropyl ether. The organic phases are combined and the solvent is removed under reduced pressure.
10.15 g of a white solid of trifluoromethanesulfonamide are thus obtained.