Hydrochloric Acid → N-[4-(4-Chlorobenzene-1-sulfonyl)phenyl]acetamide

HRID 371511Notes

Reaction equation

HRID 371511 reaction equation
[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:8]([S:9](Cl)(=[O:11])=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[Cl-:15].[Al+3].[Cl-].[Cl-].Cl>ClC1C=CC=CC=1>[Cl:15][C:5]1[CH:14]=[CH:13][C:8]([S:9]([C:8]2[CH:13]=[CH:14][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:6][CH:7]=2)(=[O:11])=[O:10])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8481N-Acetylsulfanilyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 246667N-[4-(4-Chlorobenzene-1-sulfonyl)phenyl]acetamideYield 41.6%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A mixture of 70.1 g of N-acetylsulfanilyl chloride and 60 g of aluminum chloride in 200 ml of p-chlorobenzene was heated until the evolution of hydrogen chloride ceased and then refluxed for 2 hours. The chlorobenzene was removed by decantation and the residue diluted with ether. The resulting gummy solid was recovered by filtration and treated with dilute hydrochloric acid and ethanol. The resulting solid was collected, dissolved in hot ethanol and concentrated, giving 19.31 g of the desired product as pale gray crystals, mp 187.5°-188.5° C.

Workup

  1. temperaturerefluxed for 2 hours
  2. customThe chlorobenzene was removed by decantation
  3. additionthe residue diluted with ether
  4. filtrationThe resulting gummy solid was recovered by filtration
  5. additiontreated with dilute hydrochloric acid and ethanol
  6. customThe resulting solid was collected
  7. dissolutiondissolved in hot ethanol
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-75db2537e28b4d2b8785d9db90517ca3
Source dataset
uspto-grants-1985_07
Patent number
US04532349

Reaction notes

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