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

HRID 256609

Reaction equation

HRID 256609 reaction equation
[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]

Participants

9

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 1118Sulfuric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-446eddc3b81e48e8876107b742a089a5
Source dataset
uspto-grants-1993_11
Patent number
US05258399

Linked notes

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