Water → N-(5-bromo-2-chloropyridin-3-yl)-N-methylmethanesulfonamide

HRID 241050Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 241050
[Br:1][C:2]1[CH:3]=[C:4]([NH:9][S:10]([CH3:13])(=[O:12])=[O:11])[C:5]([Cl:8])=[N:6][CH:7]=1.[C:14](=O)([O-])[O-].[K+].[K+].IC.O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([N:9]([CH3:14])[S:10]([CH3:13])(=[O:12])=[O:11])[C:5]([Cl:8])=[N:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 59519513N-(5-bromo-2-chloro-3-pyridinyl)methanesulfonamide

Produkt 1

HCID 86647824N-(5-bromo-2-chloropyridin-3-yl)-N-methylmethanesulfonamideAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of N-(5-bromo-2-chloropyridin-3-yl)methanesulfonamide (96 mg, 0.34 mmol, reagent preparation 24) in DMF (1 mL) was treated with potassium carbonate (93 mg, 0.68 mmol) and iodomethane (33 uL, 0.51 mmol) at rt for 18 h. Water was then added, and the resulting aqueous mixture was extracted twice with ethyl acetate. The combined organic extracts were washed with aqueous lithium chloride (10%) followed by water, dried over magnesium sulfate, filtered, and concentrated in vacuo to provide N-(5-bromo-2-chloropyridin-3-yl)-N-methylmethanesulfonamide (91.2 mg, 0.304 mmol, 90% yield) as a light yellow solid. 1H NMR (400 MHz, CDCl3) δ 8.46 (d, 1H), 8.00 (d, 1H), 3.32 (s, 3H), 3.07 (s, 3H); MS (EI) for C7H8BrClN2O2S: 299, 301, 303 (Br+Cl isotopes, MH+).

Aufarbeitung

  1. extractionthe resulting aqueous mixture was extracted twice with ethyl acetate
  2. washThe combined organic extracts were washed with aqueous lithium chloride (10%)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ae72cbfbfd894e9386653e91f9bb230c
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08648066B2

Notizen zur Reaktion

Wird geladen…