[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][S:10]([CH3:13])(=[O:12])=[O:11])=[C:5]([CH3:14])[CH:4]=1.[H-].[Na+].[CH3:17]I>CN(C=O)C.Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH3:17])[S:10]([CH3:13])(=[O:12])=[O:11])=[C:5]([CH3:14])[CH:4]=1To a solution of 860 mg (4.0 mmol) N-(4-methoxy-2-methyl-phenyl)-methanesulfonamide in 15 ml DMF at ambient temperature was added 192 mg (48 mmol) 60% sodium hydride dispersion and the resulting mixture was treated with 1.14 gm, 0.5 ml (8.0 mmol) methyl iodide. The reaction mixture was stirred at room temperature for 2 hours and 0.5 ml of methyl iodide was introduced and the reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was diluted with 1N HCl and then extracted with ethyl acetate. The organics were washed with brine, dried with sodium sulfate and then evaporated in vacuo to afford 293 mg (X %) of a light purple solid. Mass spectrum APCI (m/z) 230 (p+1).
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