Methyl iodide → N-(4-Methoxy-2-methyl-phenyl)-N-methyl-methanesulfonamide

HRID 1244039Notes

Reaction equation

HRID 1244039 reaction equation
[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]=1

Participants

6

Reactant 3

HCID 6328Methyl iodide2×HCID 24758Sodium hydrideHCID 15851883N-(4-methoxy-2-methylphenyl)methanesulfonamide

Product 1

HCID 21931865N-(4-Methoxy-2-methyl-phenyl)-N-methyl-methanesulfonamide

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

To 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).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 16 hours
  2. extractionextracted with ethyl acetate
  3. washThe organics were washed with brine
  4. dry with materialdried with sodium sulfate
  5. customevaporated in vacuo
  6. customto afford 293 mg (X %) of a light purple solid

Sources & evidence

ORD record
ord-d8150dc647fd4e398604cdb269f3f0a1
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

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