Hydrochloric Acid → HCID 20273665, compound

HRID 371306Notes

Reaction equation

HRID 371306 reaction equation
[C:1]1([S:7]([NH:10][C:11]2[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[Al+3].[Cl-].[Cl-].[C:22](Cl)(=[O:24])[CH3:23].Cl>ClC(Cl)C>[OH:17][C:13]1[CH:14]=[CH:15][C:16]([C:22](=[O:24])[CH3:23])=[C:11]([NH:10][S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:8])=[O:9])[CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 97359N-(3-Hydroxyphenyl)benzenesulphonamideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 20273665HCID 20273665, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent2×

Procedure

To 100 ml of dichloroethane were added 12.5 g of m-benzenesulfonamidophenol and 13.3 g of aluminum chloride and the resultant mixture was heated to 60° C. with stirring. To the mixture was added dropwise a solution of 3.6 ml of acetyl chloride dissolved in dichloroethane over a period of 2 hours followed by further heating to the same temperature for 2 hours. After allowing to cool, the mixture was placed in a hydrochloric acid acqueous solution and extracted with ethyl acetate. The extract was dried, concentrated and recrystallized from a mixture of hexane and ethyl acetate to provide 8.5 g of 4'-hydroxy-2'-benzenesulfonamidoacetophenone.

Workup

  1. temperatureby further heating to the same temperature for 2 hours
  2. temperatureto cool
  3. extractionextracted with ethyl acetate
  4. customThe extract was dried
  5. concentrationconcentrated
  6. customrecrystallized from a mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-e4ff1bbc43b9444aa51e11be32cc9401
Source dataset
uspto-grants-1985_07
Patent number
US04530899

Reaction notes

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