Methanesulfonyl chloride → N-(4-bromo-2-ethylphenyl)methanesulfonamide

HRID 859673

Reaktionsgleichung

Reaktionsgleichung von HRID 859673
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([CH2:9][CH3:10])[CH:3]=1.[CH3:11][S:12](Cl)(=[O:14])=[O:13]>N1C=CC=CC=1.CCOC(C)=O>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][S:12]([CH3:11])(=[O:14])=[O:13])=[C:4]([CH2:9][CH3:10])[CH:3]=1

Komponenten

5

Edukt 2

HCID 31297Methanesulfonyl chlorideHCID 28012834-Bromo-2-ethylaniline

Produkt 1

HCID 6469152N-(4-bromo-2-ethylphenyl)methanesulfonamideAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

4-Bromo-2-ethyl-aniline (2 mL, 14 mmol) dissolved in anhydrous pyridine (35 mL) at toom temperature was treated with methylsulfonyl chloride (1.3 mL, 16.8 mmol). The reaction was stirred at that temperature for 15 hours before it was diluted with EtOAc. The mixture was washed with H2O, brine and dried over MgSO4. The solvent was removed in vacuo and the residue was purified with flash chromatography (SiO2, 5–30% EtOAc in hexanes) to afford the desired product (3.1 g, 81% yield). 1H NMR (300 MHz, CDCl3): δ 1.25 (t, J=7.5 Hz, 3 H), 2.61–2.68 (m, 2 H), 3.02 (s, 3 H), 6.36 (s, 1 H), 7.36–7.39 (m, 3 H).

Aufarbeitung

  1. washThe mixture was washed with H2O, brine
  2. dry with materialdried over MgSO4
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified with flash chromatography (SiO2, 5–30% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-389a00c858154614be5cd1adf398aead
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07151105B2

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