Methyl iodide → N-(2-Bromophenyl)-N-methylmethanesulfonamide

HRID 472492Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 472492
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][S:9]([CH3:12])(=[O:11])=[O:10].[C:13](=O)([O-])[O-].[Cs+].[Cs+].IC>C(#N)C.ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([CH3:13])[S:9]([CH3:12])(=[O:11])=[O:10]

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 3629878N-(2-bromophenyl)methanesulfonamide

Produkt 1

HCID 67478926N-(2-Bromophenyl)-N-methylmethanesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

196 b) To a suspension of N-(2-bromo-phenyl)-methanesulfonamide (5.01 g, 20.0 mmol) and cesium carbonate (7.2 g, 22 mmol) in acetonitrile (20 mL) was added iodomethane (1.4 mL, 22 mmol). The mixture was stirred at room temperature for 24 hours then diluted with dichloromethane (30 mL), filtered through a plug of diatomaceous earth and evaporated. N-(2-Bromo-phenyl)-N-methyl-methanesulfonamide was isolated as a pale orange solid (5.22 g, 98%). 1H NMR (400 MHz, CDCl3, δ, ppm): 7.65 (d, J=8.0 Hz, 1H), 7.50 (d, J=7.9 Hz, 1H), 7.37 (t, J=7.4 Hz, 1H), 7.23 (t, J=8.2 Hz, 1H), 3.29 (s, 3H), 3.06 (s, 3H). MS=286, 288 (MH)+.

Aufarbeitung

  1. filtrationfiltered through a plug of diatomaceous earth
  2. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-4f56eed96f984dc5a0a47097350a924f
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633173B2

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