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

HRID 1272521Notes

Reaction equation

HRID 1272521 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

b)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 was heated at reflux overnight. The final mixture was concentrated and directly purified by flash chromatography over silica gel (eluting 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 hexane to DCM)

Sources & evidence

ORD record
ord-6120e816896744f9ae699066923ae09d
Source dataset
uspto-grants-2007_04
Patent number
US07208602B2

Reaction notes

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