Water → N-(3-Acetyl-4-chlorophenyl)methanesulfonamide

HRID 916684Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 916684
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.[CH3:12][S:13](Cl)(=[O:15])=[O:14].O>C1(C)C=CC=CC=1>[C:8]([C:6]1[CH:7]=[C:2]([NH:1][S:13]([CH3:12])(=[O:15])=[O:14])[CH:3]=[CH:4][C:5]=1[Cl:11])(=[O:10])[CH3:9]

Komponenten

5

Edukt 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 15019111-(5-amino-2-chlorophenyl)ethanone

Produkt 1

HCID 22141405N-(3-Acetyl-4-chlorophenyl)methanesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

1-(5-Amino-2-chlorophenyl)ethanone (411 mg; synthesized by the process reported by Radziejewski et al., Heterocycles, vol. 26, pp. 1227-1238, 1987) was dissolved in toluene (5 mL), and pyridine(235 μL) and methanesulfonyl chloride (225 μL) were added. The resulting mixture was stirred at room temperature for 50 minutes. After adding water (50 mL), the reaction mixture was extracted with ethyl acetate (50 mL). The organic layer was washed with an aqueous 1 N hydrochloric acid solution (50 mL) and saturated brine (50 mL) and then dried over anhydrous sodium sulfate (5 g). The solvent was distilled off under reduced pressure to yield N-(3-acetyl-4-chlorophenyl)methanesulfonamide (595 mg) as a colorless crystal.

Aufarbeitung

  1. customsynthesized by the process
  2. extractionthe reaction mixture was extracted with ethyl acetate (50 mL)
  3. washThe organic layer was washed with an aqueous 1 N hydrochloric acid solution (50 mL) and saturated brine (50 mL)
  4. dry with materialdried over anhydrous sodium sulfate (5 g)
  5. distillationThe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-87ee12540e464469bf8c40aac6beee7c
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07271190B2

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