Methyl iodide → N-(3-bromophenyl)-N-methylmethanesulfonamide

HRID 472446Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 472446
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[C:13](=O)([O-])[O-].[K+].[K+].IC>CC(C)=O.ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([N:8]([CH3:13])[S:9]([CH3:12])(=[O:10])=[O:11])[CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 798932N-(3-bromophenyl)methanesulfonamide

Produkt 1

HCID 57584791N-(3-bromophenyl)-N-methylmethanesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a suspension of N-(3-bromo-phenyl)-methanesulfonamide (1.0 g, 4.0 mmol) and potassium carbonate (0.61 g, 4.4 mmol) in acetone (10 mL) was added iodomethane (0.30 mL, 4.8 mmol). The mixture was stirred at room temperature for 18 hours, diluted with dichloromethane (30 mL), filtered through a plug of diatomaceous earth and evaporated under reduced pressure. N-(3-Bromo-phenyl)-N-methyl-methanesulfonamide was isolated a tan viscous oil (1.08 g, 100%). 1H NMR (400 MHz, CDCl3, δ, ppm): 7.53 (s, 1H), 7.43 (d, J=7.9 Hz, 1H), 7.35 (d, J=8.2 Hz, 1H), 7.29-7.23 (m, 1H), 3.32 (s, 3H), 2.86 (s, 3H). MS=286, 288 (MH)+.

Aufarbeitung

  1. filtrationfiltered through a plug of diatomaceous earth
  2. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-83dee764846943b3b297d56e6d0c303e
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633173B2

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