Methyl iodide → N-(4-Iodophenyl)-N-methylmethanesulphonamide

HRID 1084964

Reaction equation

HRID 1084964 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[CH:4][CH:3]=1.[OH-].[Na+].IC.Cl[CH2:18]Cl>S(=O)(=O)(O)[O-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[I:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH3:18])[S:9]([CH3:12])(=[O:11])=[O:10])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 836147N-(4-iodophenyl)methanesulfonamide

Product 1

HCID 13920676N-(4-Iodophenyl)-N-methylmethanesulphonamide

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent

Procedure

A mixture of N-(4-iodophenyl)methanesulphonamide (4.3 g), 50% aqueous sodium hydroxide (25 ml), iodomethane (5 ml), dichloromethane (10 ml) and tetrabutylammonium bisulphate (0.5 g) was stirred vigorously for 2 h. Water (50 ml) was added and the mixture was extracted with ether (3×50 ml). The organic extracts were washed with water and brine, dried and concentrated to a solid which was triturated with hexane to give the title compound as white crystals (4.1 g) m.p. 106°-107°.

Workup

  1. extractionthe mixture was extracted with ether (3×50 ml)
  2. washThe organic extracts were washed with water and brine
  3. customdried
  4. concentrationconcentrated to a solid which
  5. customwas triturated with hexane

Sources & evidence

ORD record
ord-aa37564c3684402494b752931c2644fa
Source dataset
uspto-grants-1991_04
Patent number
US05006556

Linked notes

Loading…