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

HRID 466356Notes

Reaction equation

HRID 466356 reaction equation
[C:1]([C:4]1[CH:14]=[CH:13][CH:12]=[CH:11][C:5]=1[NH:6][S:7]([CH3:10])(=[O:9])=[O:8])(=[O:3])[CH3:2].[H-].[Na+].CI.[C:19](OCC)(=O)C>O1CCCC1.CN(C)C=O>[O:3]=[C:1]([C:4]1[CH:14]=[CH:13][CH:12]=[CH:11][C:5]=1[N:6]([CH3:19])[S:7]([CH3:10])(=[O:8])=[O:9])[CH3:2]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 2767200N-(2-acetylphenyl)methanesulfonamide

Product 1

HCID 19873387N-(2-acetylphenyl)-N-methylmethanesulfonamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

2'-Acetylmethanesulfonanilide (1.0 g, 4.7 mmol) in 10 ml tetrahydrofuran is reacted with 0.23 g (4.8 mmol) of 50% sodium hydride dispersion in mineral oil at 5° C. for 15 min. Methyl iodide (1.5 g, 10.56 mmol) in 10 ml of dimethylformamide is added over 15 min at 0°-10° C. and stirred in cold for 15 min. Dimethylformamide (10 ml) is added, and the reaction is stirred for 2 days at room temperature. The reaction is taken up into ethyl acetate, the organic layer washed with water, sodium carbonate solution, water, and saturated sodium chloride successively. The dried organic layer is evaporated and the product crystallized from ether-pet. ether; m.p. 98°-99° C.

Workup

  1. stirringthe reaction is stirred for 2 days at room temperature
  2. washthe organic layer washed with water, sodium carbonate solution, water, and saturated sodium chloride successively
  3. customThe dried organic layer is evaporated
  4. customthe product crystallized from ether-pet. ether

Sources & evidence

ORD record
ord-1b06c96958d546a188a3816ad364e196
Source dataset
uspto-grants-1992_10
Patent number
US05155268

Reaction notes

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