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

HRID 947

Reaction equation

HRID 947 reaction equation
[F:1][C:2]([F:8])([F:7])[S:3]([NH2:6])(=[O:5])=[O:4].[F:9][C:10](=[C:15]([F:17])[F:16])[CH2:11][C:12](Cl)=[O:13]>[OH-].[Na+]>[F:9][C:10](=[C:15]([F:17])[F:16])[CH2:11][C:12]([NH:6][S:3]([C:2]([F:8])([F:7])[F:1])(=[O:5])=[O:4])=[O:13]

Participants

4

Reactant 2

HCID 79001TrifluoromethylsulfonamideHCID 109207893,4,4-Trifluoro-3-butenoyl chloride

Product 1

HCID 153350263,4,4-trifluoro-N-[(trifluoromethyl)sulfonyl]-3-butenamideYield 16.4%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

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.

Workup

  1. stirringThe mixture was stirred in cold for 30 min
  2. customthe white precipitate formed
  3. filtrationwas filtered
  4. washwashed with cold water (10 mL)
  5. customdried

Sources & evidence

ORD record
ord-e1a0dc1a113c454bac338b6a5d18d9a1
Source dataset
uspto-grants-1998_03
Patent number
US05723470

Linked notes

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