Methyl iodide → HCID 56980471, compound

HRID 1453055Notes

Reaction equation

HRID 1453055 reaction equation
CI.[Br:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])=[CH:6][CH:5]=1.[C:15](=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]([CH3:15])[S:11]([CH3:14])(=[O:13])=[O:12])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 706841N-(4-Bromophenyl)methanesulfonamide

Product 1

HCID 56980471HCID 56980471, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl iodide (2.38 g, 0.0382M) was added to a mixture of N-(4-bromophenyl)methanesulfonamide (6.37 g, 0.0255M) and potassium carbonate (5.21 g, 0.0382M) in dimethylformamide (50 ml) at room temperature under an atmosphere of nitrogen. The reaction mixture was stirred for a further 24 hrs after which time it was partitioned between diethylether (100 ml) and water (100 ml). The aqueous was extracted further with diethyl ether (2×100 ml). The combined organics were dried over magnesium sulfate, filtered and the solvent concentrated in vacuuo to afford the title compound as a white solid (5.6 g). 1H NMR (CDCl3): 2.94 (s, 3H), 3.04 (s, 3H), 6.89 (d, J=2.56 Hz, 2H), 7.30 (d, J=2.56 Hz, 2H),).

Workup

  1. customwas partitioned between diethylether (100 ml) and water (100 ml)
  2. extractionThe aqueous was extracted further with diethyl ether (2×100 ml)
  3. dry with materialThe combined organics were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe solvent concentrated in vacuuo

Sources & evidence

ORD record
ord-6e5a0ff278044cd4ac3158b553f979e7
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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