Methyl iodide → N-cyclopropyl-N-methyl-2-nitrobenzenesulfonamide

HRID 1879639Notes

Reaction equation

HRID 1879639 reaction equation
[CH:1]1([NH:4][S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N+:14]([O-:16])=[O:15])(=[O:7])=[O:6])[CH2:3][CH2:2]1.[C:17](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O>[CH:1]1([N:4]([CH3:17])[S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N+:14]([O-:16])=[O:15])(=[O:7])=[O:6])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 796630N-cyclopropyl-2-nitrobenzenesulfonamide

Product 1

HCID 47169839N-cyclopropyl-N-methyl-2-nitrobenzenesulfonamideYield 89.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of N-cyclopropyl-2-nitrobenzenesulfonamide (5.63 g), potassium carbonate (4.82 g) and N,N-dimethylformamide (60 mL), methyl iodide (2.17 mL) was added and stirred at room temperature for 6 hours. The reaction mixture was evaporated under reduced pressure, and the residue was diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue was purified by silica gel column chromatography (eluent; n-hexane:diethyl ether=1:0-1:1) to give N-cyclopropyl-N-methyl-2-nitrobenzenesulfonamide (5.35 g) as a brown solid.

Workup

  1. additionwas added
  2. customThe reaction mixture was evaporated under reduced pressure
  3. additionthe residue was diluted with water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationby distilling off the solvent under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluent; n-hexane:diethyl ether=1:0-1:1)

Sources & evidence

ORD record
ord-4f791ea3186942b3978244b86ed62b3f
Source dataset
uspto-grants-2012_11
Patent number
US08318702B2

Reaction notes

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