Iodine → N-(4-iodo-3-methylphenyl)-N-methylmethanesulphonamide

HRID 2254668

Reaktionsgleichung

Reaktionsgleichung von HRID 2254668
[CH3:1][N:2]([C:7]1[CH:8]=[C:9]([CH3:13])[CH:10]=[CH:11][CH:12]=1)[S:3]([CH3:6])(=[O:5])=[O:4].II.[I:16](O)(=O)=O.C(=O)(O)[O-].[Na+]>C(O)(=O)C.S(=O)(=O)(O)O.O.C(OCC)(=O)C>[I:16][C:10]1[CH:11]=[CH:12][C:7]([N:2]([CH3:1])[S:3]([CH3:6])(=[O:4])=[O:5])=[CH:8][C:9]=1[CH3:13]

Komponenten

9

Edukt 4

HCID 807IodineHCID 24345Iodic acidHCID 516892Sodium BicarbonateHCID 19785598N-Methyl-N-(3-tolyl)methanesulphonamide

Produkt 1

HCID 19785617N-(4-iodo-3-methylphenyl)-N-methylmethanesulphonamideAusbeute 340 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittelHCID 1118Sulfuric AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of N-methyl-N-(3-tolyl)methanesulphonamide (0.12 g), iodine (76 g) and iodic acid (35 mg) in glacial acetic acid (5 ml) and concentrated sulphuric acid (0.6 ml) was stirred at 80° C. for 2.5 hours. Ethyl acetate (40 ml) and water (40 ml) were then added and the mixture neutralised with solid sodium bicarbonate. The organic phase was washed with brine (30 ml), dried (MgSO4) and the solvent evaporated to leave N-(4-iodo-3-methylphenyl)-N-methylmethanesulphonamide (0.22 g, 90%), m.p. 85°-87° C.

Aufarbeitung

  1. washThe organic phase was washed with brine (30 ml)
  2. dry with materialdried (MgSO4)
  3. customthe solvent evaporated

Quellen und Nachweise

ORD-Eintrag
ord-2ef0909f59a044baa0c31e4730d78f1d
Quelldatensatz
uspto-grants-1993_08
Patentnummer
US05236948

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