2-Nitroaniline → NITROBENZENE2NNBISMETHYLSULFONYL

HRID 629194Notes

Reaction equation

HRID 629194 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].[H-].[Na+].[CH3:13][S:14](Cl)(=[O:16])=[O:15]>CN(C)C=O.O>[CH3:13][S:14]([N:6]([C:5]1[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=1[N+:1]([O-:3])=[O:2])[S:14]([CH3:13])(=[O:16])=[O:15])(=[O:16])=[O:15]

Participants

6

Reactant 3

HCID 69462-NitroanilineHCID 24758Sodium hydrideHCID 31297Methanesulfonyl chloride

Product 1

HCID 296455NITROBENZENE2NNBISMETHYLSULFONYLYield 70.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a cooled (0° C.) solution of 2-nitroaniline (1 g, 7.25 mmol) in dimethylformamide (DMF, 10 mL) was added sodium hydride (608 mg, 25 mmol). After addition was complete methanesulfonyl chloride (1.69 mL, 21.8 mmol) was added and the reaction was warmed to room temperature and stirred for 1 hour. The reaction was then diluted with water and the product extracted with ethyl acetate. The organic layer was concentrated and purified by chromatography to provide N-(methylsulfonyl)-N-(2-nitrophenyl)methanesulfonamide (1.5 g, 70% yield). 1H NMR (400 MHz, DMSO-d6) δ 8.17 (s, 1H), 7.89 (m, 1H), 7.80 (m, 2H), 3.58 (s, 6H).

Workup

  1. additionAfter addition
  2. additionwas added
  3. extractionthe product extracted with ethyl acetate
  4. concentrationThe organic layer was concentrated
  5. custompurified by chromatography

Sources & evidence

ORD record
ord-3a81c803fa364dfca973ef38cd0d5866
Source dataset
uspto-grants-2016_04
Patent number
US09315494B2

Reaction notes

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