Triethylamine → 2-(2,2-Difluoroethylthio)-phenylsulfonamide

HRID 373447Notes

Reaction equation

HRID 373447 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].Br[CH2:20][CH:21]([F:23])[F:22]>CO>[F:22][CH:21]([F:23])[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

5

Reactant 3

HCID 8471TriethylamineHCID 1361862-Bromo-1,1-difluoroethaneHCID 110415322-Sulfanylbenzene-1-sulfonamide

Product 1

HCID 109560712-(2,2-Difluoroethylthio)-phenylsulfonamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 145.2 g of the triethylamine salt of 2-mercaptophenylsulfonamide obtained in accordance with Example P6 and 79.7 g of 2-bromo-1,1-difluoroethane in 600 ml of methanol is stirred for 16 hours at a temperature of from +55° C. to +60° C. The reaction mixture is then concentrated by evaporation. The residue is stirred with ice-water and the resulting suspension is filtered to yield 120 g (95% of the theoretical yield) of 2-(2,2-difluoroethylthio)-phenyl-sulfonamide having a melting point of from +111° C. to +112° C.

Workup

  1. concentrationThe reaction mixture is then concentrated by evaporation
  2. stirringThe residue is stirred with ice-water
  3. filtrationthe resulting suspension is filtered
  4. customto yield 120 g (95% of the

Sources & evidence

ORD record
ord-53ce542ea4f04c3fa3951f8d0d4beaee
Source dataset
uspto-grants-1992_11
Patent number
US05163996

Reaction notes

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