N-Acetylsulfanilyl chloride → Benzenesulfonyl fluoride, 4-(acetylamino)-

HRID 1764049Notes

Reaction equation

HRID 1764049 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[F-:15].[K+]>O>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([F:15])(=[O:13])=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 8481N-Acetylsulfanilyl chlorideHCID 522689Potassium Fluoride

Product 1

HCID 67608Benzenesulfonyl fluoride, 4-(acetylamino)-Yield 28.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

60 gm (.257 mole) of p-acetamidobenzenesulfonyl chloride was added to 15 ml water and stirred to form a thick paste. 20 gm (.416 mole) of potassium fluoride dissolved in 25 ml water was added and the resulting slurry was heated for one hour in an oil bath at reflux. After one hour the slurry was cooled, filtered, washed with ice water and dried by suction. The crude product was recrystallized from 95% ethanol to give 16 gm of p-acetamidobenzenesulfonyl fluoride mp 169°-171° C; literature value 171° C.

Workup

  1. customto form a thick paste
  2. additionwas added
  3. temperaturethe resulting slurry was heated for one hour in an oil bath
  4. temperatureat reflux
  5. temperatureAfter one hour the slurry was cooled
  6. filtrationfiltered
  7. washwashed with ice water
  8. customdried by suction
  9. customThe crude product was recrystallized from 95% ethanol

Sources & evidence

ORD record
ord-ab04d2a3c93e433db8a574a00fc60971
Source dataset
uspto-grants-1978_09
Patent number
US04115059

Reaction notes

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