Benzenesulfonamide, 2-(3,3,3-trifluoro-1-propenyl)- → 2-(3,3,3-Trifluoropropyl)benzenesulfonamide

HRID 652385Notes

Reaction equation

HRID 652385 reaction equation
[F:1][C:2]([F:16])([F:15])[CH:3]=[CH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11]([NH2:14])(=[O:13])=[O:12].[H][H]>[Pd].C(OCC)(=O)C>[F:16][C:2]([F:1])([F:15])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11]([NH2:14])(=[O:13])=[O:12]

Participants

5

Reactant 2

HCID 53741182Benzenesulfonamide, 2-(3,3,3-trifluoro-1-propenyl)-HCID 178418361HCID 178418361, compound

Product 1

HCID 110104802-(3,3,3-Trifluoropropyl)benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 50.2 g of 2-(3,3,3-trifluoro-1-propenyl)-phenylsulfonamide, 500 ml of ethyl acetate and 5 g of a 5% Pd/C catalyst is shaken for 1/2 hour at 20°-25° C. in a hydrogen atmosphere. The catalyst is then filtered off, the mixture is concentrated by evaporation, and the residue is crystallised from a mixture of methylene chloride and ether to thus yield 49.6 g of 2-(3,3,3-trifluoropropyl)-phenylsulfonamide, m.p. 148°-149° C.

Workup

  1. filtrationThe catalyst is then filtered off
  2. concentrationthe mixture is concentrated by evaporation
  3. customthe residue is crystallised from a mixture of methylene chloride and ether to thus yield 49.6 g of 2-(3,3,3-trifluoropropyl)-phenylsulfonamide, m.p. 148°-149° C.

Sources & evidence

ORD record
ord-e22fcaab28dd42379240c0162d2d7006
Source dataset
uspto-grants-1987_06
Patent number
US04671819

Reaction notes

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