2-Fluoroethyl bromide → 2-(2-Fluoroethylthio)-phenylsulfonamide

HRID 374350Notes

Reaction equation

HRID 374350 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][CH2:21][F:22]>O1CCCC1>[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 129822-Fluoroethyl bromideHCID 198097532-Mercaptophenylsulfonamide triethylamine salt

Product 1

HCID 198097542-(2-Fluoroethylthio)-phenylsulfonamideYield 571.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 29 g of the 2-mercaptophenylsulfonamide triethylamine salt obtained in accordance with Example H6 and 2 g of 2-bromo-1-fluoroethane in 130 ml of tetrahydrofuran is stirred for 6 hours at a temperature of +40° C. to +45° C. The reaction mixture is then cooled to 0° C. and filtered. The filtrate is evaporated and the resulting residue is crystallized from methylene dichloride to give 21.2 g (90.2% of theory) of 2-(2-fluoroethylthio)-phenylsulfonamide having a melting point of +84° to +85° C.

Workup

  1. filtrationfiltered
  2. customThe filtrate is evaporated
  3. customthe resulting residue is crystallized from methylene dichloride

Sources & evidence

ORD record
ord-1fb3128e46c04bed8f76a416cf3704e2
Source dataset
uspto-grants-1992_11
Patent number
US05166430

Reaction notes

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