Methyl iodide → N-(3-bromophenyl)-N-methylmethanesulfonamide

HRID 18421Notes

Reaction equation

HRID 18421 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[C:13](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([N:8]([CH3:13])[S:9]([CH3:12])(=[O:10])=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 798932N-(3-bromophenyl)methanesulfonamide

Product 1

HCID 57584791N-(3-bromophenyl)-N-methylmethanesulfonamideYield 90.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-(3-bromophenyl)methanesulfonamide (5.15 g, 20.6 mmol, Combi-Blocks) in dry dimethylformamide (100 ml) was treated with potassium carbonate (4.3 g, 31.2 mmol) at room temperature with stirring under argon. After stirring for 10 minutes methyl iodide (2.9 g, 20.6 mmol) was added dropwise over 5 minutes and stirring continued at room temperature for 1 h. The reaction mixture was partitioned between ethyl acetate (250 ml), and water (3×150 ml). The organic layer was dried over sodium sulphate and the solvent removed under reduced pressure to give the title compound as a brown oil (4.90 g, 90%); 1H-NMR (400 MHz, CDCl3): 2.86 (3H, s), 3.32 (3H, s), 7.26 (1H, m), 7.35 (1H, m), 7.43 (1H, m), 7.53 (1H, m).

Workup

  1. additionwas added dropwise over 5 minutes
  2. stirringstirring
  3. customThe reaction mixture was partitioned between ethyl acetate (250 ml), and water (3×150 ml)
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-deaa39f6e9d8417ca80c6026aac200f4
Source dataset
uspto-grants-2010_06
Patent number
US07741351B2

Reaction notes

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