1-Chloro-2-fluoroethane → 2-(2-Fluoroethylthio)-phenylsulfonamide

HRID 374349

Reaction equation

HRID 374349 reaction equation
C(N(CC)CC)C.[SH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15]([NH2:18])(=[O:17])=[O:16].Cl[CH2:20][CH2:21][F:22]>CO>[F:22][CH2:21][CH2:20][S:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15]([NH2:18])(=[O:17])=[O:16]

Participants

4

Reactant 2

HCID 129831-Chloro-2-fluoroethaneHCID 198097532-Mercaptophenylsulfonamide triethylamine salt

Product 1

HCID 198097542-(2-Fluoroethylthio)-phenylsulfonamideYield 74.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5.8 g of the 2-mercaptophenylsulfonamide triethylamine salt obtained in accordance with Example H6 and 1.7 g of 2-chloro-1-fluoroethane in 40 ml of methanol is stirred in a bomb tube for 23 hours at a temperature of +50° to +55° C. The reaction mixture is then evaporated and water is added to the residue which remains. The mixture is extracted with ethyl acetate, and the organic phase is washed and dried. Evaporation of the solution gives 3.5 g of 2-(2-fluoroethylthio)-phenylsulfonamide (74.5% of theory) having a melting point of +83° to +85° C.

Workup

  1. customThe reaction mixture is then evaporated
  2. additionwater is added to the residue which
  3. extractionThe mixture is extracted with ethyl acetate
  4. washthe organic phase is washed
  5. customdried
  6. customEvaporation of the solution

Sources & evidence

ORD record
ord-ed4db594ab6449c09e87eb753c4cf549
Source dataset
uspto-grants-1992_11
Patent number
US05166430

Linked notes

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