Methyl iodide → HCID 58521929, compound

HRID 2390253Notes

Reaction equation

HRID 2390253 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:9][S:10]([CH3:13])(=[O:12])=[O:11])[CH:5]=[CH:6][C:7]=1[CH3:8].[H-].[Na+].I[CH3:17]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([N:9]([CH3:17])[S:10]([CH3:13])(=[O:12])=[O:11])[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59770082HCID 59770082, compound2×

Product 1

HCID 58521929HCID 58521929, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-(3-bromo-4-methylphenyl)methanesulfonamide (Intermediate 196, step 1; 710 mg; 2.69 mmol) in anhydrous DMF (14 mL) was treated with NaH (129 mg; 3.23 mmol) followed after 5 minutes by treatment with iodomethane (200 μl; 3.23 mmol). The reaction mixture was stirred for 16 hours, then quenched with a 5 N solution of NaOH in water. The reaction mixture was stirred for few minutes and extracted with EtOAc. The organic phase was washed with water and brine, dried over MgSO4 and concentrated to dryness affording the title compound as a brown sticky solid (730 mg, 98%).

Workup

  1. customquenched with a 5 N solution of NaOH in water
  2. stirringThe reaction mixture was stirred for few minutes
  3. extractionextracted with EtOAc
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-5ce9f0f5b62c40e29310a32e298685ce
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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