p-Aminoacetophenone → N-(4-acetylphenyl)methanesulfonamide

HRID 238929

Reaction equation

HRID 238929 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[CH3:11][S:12](Cl)(=[O:14])=[O:13]>N1C=CC=CC=1.O>[CH3:11][S:12]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1)(=[O:14])=[O:13]

Participants

5

Reactant 2

HCID 7468p-AminoacetophenoneHCID 31297Methanesulfonyl chloride

Product 1

HCID 684083N-(4-acetylphenyl)methanesulfonamideYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

A cooled solution of 4′-aminoacetophenon (10 mmol) in pyridine (10 mL) at 0° C. was treated with methanesulfonyl chloride (15 mmol) and stirred at room temperature for 2 h. The reaction mixture was diluted with H2O and extracted with EtOAc several times. The combined organic layers were washed with H2O and brine, dried over MgSO4, filtered, and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using EtOAc:hexanes to afford 4′-(Methylsulfonylamino)acetophenone (13-5, LJO-298).

Workup

  1. extractionextracted with EtOAc several times
  2. washThe combined organic layers were washed with H2O and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-ce529ee51da142f182b51d887ecae8d4
Source dataset
uspto-grants-2014_02
Patent number
US08642657B2

Linked notes

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