Methyl iodide → N-Methyl-N-(2-nitrophenyl)methanesulfonamide

HRID 629195Notes

Reaction equation

HRID 629195 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][S:11]([CH3:14])(=[O:13])=[O:12])([O-:3])=[O:2].[H-].[Na+].I[CH3:18]>CN(C=O)C>[CH3:18][N:10]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])[S:11]([CH3:14])(=[O:13])=[O:12]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 296454N-(2-nitrophenyl)methanesulfonamide

Product 1

HCID 13314625N-Methyl-N-(2-nitrophenyl)methanesulfonamideYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cooled (0° C.) solution of N-(2-nitrophenyl)methanesulfonamide (50 mg, 0.231 mmol) in DMF (2 mL) was added sodium hydride (11 mg, 0.46 mmol) and the reaction was warmed to room temperature and stirred for 20 minutes. The reaction was then re-cooled to 0° C. and iodomethane (0.029 mL 0.46 mmol) was added. The reaction was warmed to room temperature and stirred for 3 hours. The crude reaction was concentrated and purified by silica gel chromatography to provide N-methyl-N-(2-nitrophenyl)methanesulfonamide (20 mg, 38% yield). 1H NMR (300 MHz, CDCl3) δ 7.91 (m, 1H), 7.70-7.50 (m, 3H), 3.34 (s, 3H), 3.01 (s, 3H).

Workup

  1. temperatureThe reaction was then re-cooled to 0° C.
  2. temperatureThe reaction was warmed to room temperature
  3. stirringstirred for 3 hours
  4. customThe crude reaction
  5. concentrationwas concentrated
  6. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-0a0c419b87e24a608182d6b306ff999a
Source dataset
uspto-grants-2016_04
Patent number
US09315494B2

Reaction notes

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