Water → 2',4'-Dinitro-N-methoxy-p-toluenesulfonanilide

HRID 1356629Notes

Reaction equation

HRID 1356629 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:7]=1[NH:15][O:16][CH3:17])([O-:5])=[O:4].[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1.O>CN(C=O)C>[N+:3]([C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:7]=1[N:15]([O:16][CH3:17])[S:24]([C:21]1[CH:22]=[CH:23][C:18]([CH3:28])=[CH:19][CH:20]=1)(=[O:26])=[O:25])([O-:5])=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 12102671N-Methoxy-2,4-dinitroaniline

Product 1

HCID 185092272',4'-Dinitro-N-methoxy-p-toluenesulfonanilideYield 21%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (60%, 0.24 g (6.00 mmol)) in DMF (8.0 ml), N-(2,4-dinitrophenyl)-O-methylhydroxylamine (0.85 g (3.99 mmol)) was added under ice-cooling with stirring. After 15 minutes' stirring under ice-cooling, p-toluenesulfonyl chloride (1.15 g (6.03 mmol)) was added. Then, the temperature of the reaction mixture was brought to room temperature and stirred at the same temperature for 18 hours. The reaction mixture was then poured into water and extracted with ethyl acetate. The extract was washed with water and saturated sodium chloride solution, successively, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel chromatography with ethyl acetate-hexane (1:3) as eluent, to give 0.30 g (21%) of the title compound as orange crystals.

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. stirringAfter 15 minutes' stirring under ice-
  4. temperaturecooling
  5. customwas brought to room temperature
  6. stirringstirred at the same temperature for 18 hours
  7. extractionextracted with ethyl acetate
  8. washThe extract was washed with water and saturated sodium chloride solution
  9. dry with materialsuccessively, dried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-609c45b5eb004e8e99db656ed090a683
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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