4-Chlorobenzenesulfonyl chloride → 2,2,2-Trifluoroethane-1-sulfonamide

HRID 853774Notes

Reaction equation

HRID 853774 reaction equation
[F:1][C:2]([F:11])([F:10])[CH2:3]N1CCCCC1.C([N:14](CC)CC)C.ClC1C=CC([S:26](Cl)(=[O:28])=[O:27])=CC=1>ClCCCl>[F:1][C:2]([F:11])([F:10])[CH2:3][S:26]([NH2:14])(=[O:28])=[O:27]

Participants

5

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 178400041-(2,2,2-Trifluoroethyl)piperidine

Product 1

HCID 212655462,2,2-Trifluoroethane-1-sulfonamideYield 114.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of O-protected trifluoroethyl piperidine (1.13 g, 3.6 mmol) in DCE (15 mL) was added triethylamine (0.6 mL, 4.3 mmol) then 4-chlorobenzenesulfonyl chloride (1.13 g, 5.4 mmol) and the reaction mixture was heated at reflux overnight. The final mixture was concentrated and directly purified by flash chromatography over silica gel (eluting with hexane to DCM) to afford 0.67 g (38%) of O-protected trifluoroethyl sulfonamide.

Workup

  1. temperatureat reflux overnight
  2. concentrationThe final mixture was concentrated
  3. customdirectly purified by flash chromatography over silica gel (eluting with hexane to DCM)

Sources & evidence

ORD record
ord-6f48be7f0b274a12b71403a5aec730ef
Source dataset
uspto-grants-2007_08
Patent number
US07256186B2

Reaction notes

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