Reaction #1043

Reaction equation

trifluoromethanesulfonamide

3,4,4-trifluoro-3-butenoyl chloride

→

desired product

Yield 16.4%

3,4,4-trifluoro-N-[(trifluoromethyl)sulfonyl]-3-butenamide

Yield 16.4%

Solvents

sodium hydroxide

Conditions

Workup

1. 1
   workup.STIRRINGThe mixture was stirred in cold for 30 min
2. 2
   Otherthe white precipitate formed
3. 3
   Filtrationwas filtered
4. 4
   Washwashed with cold water (10 mL)
5. 5
   Otherdried

Procedure

To an ice-cooled solution of trifluoromethanesulfonamide (2.75 g, 18.4 mmol) in 7.4 mL of 2.5 N sodium hydroxide was added 3,4,4-trifluoro-3-butenoyl chloride (2.93 g, 18.5 mmol) with stirring in 2 min. The mixture was stirred in cold for 30 min and the white precipitate formed was filtered, washed with cold water (10 mL) and dried to give 0.82 g (16%) of the desired product as a white solid. m.p. 115°-120° C.

Source