Pyridine → N-(4-acetylphenyl)methanesulfonamide

HRID 10720

Reaktionsgleichung

Reaktionsgleichung von HRID 10720
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][CH:5]=1)=[O:3].N1C=CC=CC=1.[S:17](Cl)([CH3:20])(=[O:19])=[O:18]>ClCCl>[C:2]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][S:17]([CH3:20])(=[O:19])=[O:18])=[CH:6][CH:5]=1)(=[O:3])[CH3:1]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 7468p-AminoacetophenoneHCID 31297Methanesulfonyl chloride

Produkt 1

HCID 684083N-(4-acetylphenyl)methanesulfonamideAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Ex-100A: A solution of 4-aminoacetophenone (5.0 g, 37.0 mmol) and pyridine (3.0 mL) in anhydrous dichloromethane (300 mL) was treated with mesyl chloride (2.86 mL, 37.0 mmol). The reaction was stirred for 84 hours at room temperature under nitrogen, and then quenched with saturated NH4Cl solution (100 mL). The organic phase was collected, washed with water (100 mL) and brine, dried over sodium sulfate, and concentrated over silica. The material was purified by silica gel chromatography (50% ethyl acetate/hexanes) to give 4.72 g (60%) of N-(4-acetyl-phenyl)-methanesulfonamide as a yellowish oil. 1H-NMR (DMSO-d6) δ 10.28 (s, 1H), 7.90 (d, 1H), 7.24 (d, 1H), 3.06 (s, 3H), 2.48 (s, 3H).

Aufarbeitung

  1. customquenched with saturated NH4Cl solution (100 mL)
  2. customThe organic phase was collected
  3. washwashed with water (100 mL) and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated over silica
  6. customThe material was purified by silica gel chromatography (50% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-4e657d09667144e7a75208f9bb28d3d5
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094801B2

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