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

HRID 238929

Reaktionsgleichung

Reaktionsgleichung von HRID 238929
[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]

Komponenten

5

Edukt 2

HCID 7468p-AminoacetophenoneHCID 31297Methanesulfonyl chloride

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1049PyridineLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-ce529ee51da142f182b51d887ecae8d4
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642657B2

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