1,2-Dichloro-1-fluoroethane → 2-(2-Chloro-2-fluoroethylthio)-phenylsulfonamide

HRID 374352Notes

Reaction equation

HRID 374352 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:19][CH:20]([F:23])[CH2:21]Cl>CO>[Cl:19][CH:20]([F:23])[CH2:21][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 790041,2-Dichloro-1-fluoroethaneHCID 198097532-Mercaptophenylsulfonamide triethylamine salt

Product 1

HCID 190867512-(2-Chloro-2-fluoroethylthio)-phenylsulfonamideYield 49.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 217.8 g of the 2-mercaptophenylsulfonamide triethylamine salt obtained in accordance with Example H6 and 101 g of 1,2-dichloro-1-fluoroethane in 950 ml of methanol is stirred for 24 hours at a temperature of +65° C. to +70° C. and is then stirred in an autoclave for a further 24 hours at +95° C. to +100° C. The reaction mixture is then evaporated and the residue is triturated with water. Extracting the mixture with ethyl acetate, washing the extract with water, drying it over sodium sulfate and evaporating it and purifying the residue by chromatography with methylene chloride gives 99.5 g (49.2% of theory) of 2-(2-chloro-2-fluoroethylthio)-phenylsulfonamide having a melting point of +88° C. to +89° C.

Workup

  1. stirringis then stirred in an autoclave for a further 24 hours at +95° C. to +100° C
  2. customThe reaction mixture is then evaporated
  3. customthe residue is triturated with water
  4. extractionExtracting the mixture with ethyl acetate
  5. washwashing the
  6. extractionextract with water
  7. dry with materialdrying it over sodium sulfate
  8. customevaporating it
  9. custompurifying the residue by chromatography with methylene chloride

Sources & evidence

ORD record
ord-f06dd4e54b284f768e15c50d816a7db2
Source dataset
uspto-grants-1992_11
Patent number
US05166430

Reaction notes

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