1-Chloro-2,4-Dinitrobenzene → 2-Chloro-2',4'-dinitro-N-methoxybenzenesulfonanilide

HRID 1356687Notes

Reaction equation

HRID 1356687 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][O:14][CH3:15])(=[O:12])=[O:11].[N+:16]([C:19]1[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[CH:21][C:20]=1Cl)([O-:18])=[O:17].O>CN(C=O)C>[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([N:13]([O:14][CH3:15])[C:20]1[CH:21]=[CH:22][C:23]([N+:25]([O-:27])=[O:26])=[CH:24][C:19]=1[N+:16]([O-:18])=[O:17])(=[O:12])=[O:11]

Participants

6

Reactant 4

HCID 61-Chloro-2,4-DinitrobenzeneHCID 962WaterHCID 24758Sodium hydrideHCID 185093192-chloro-N-methoxybenzenesulfonamide

Product 1

HCID 185093092-Chloro-2',4'-dinitro-N-methoxybenzenesulfonanilideYield 62.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (60%, 0.09 g (2.25 mmol)) in DMF (3.0 ml), 2-chloro-N-methoxybenzenesulfonamide (0.48 g (2.17 mmol)) was added with stirring under cooling with ice. To the resulting mixture, after 15 minutes' stirring under cooling with ice, 2,4-dinitrochlorobenzene (0.41 g (2.02 mmol)) was added. The resulting mixture was then stirred under cooling with ice for one hour and at room temperature for one hour. Water was added to the reaction mixture and the resulting mixture was extracted with diethyl ether. The extract was washed with water, dilute hydrochloric acid and a saturated aqueous solution of sodium chloride, successively, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure, to give 0.49 g (62%) of the title compound as pale yellow crystals.

Workup

  1. additionwas added
  2. temperatureunder cooling with ice
  3. stirringTo the resulting mixture, after 15 minutes' stirring
  4. additionwas added
  5. stirringThe resulting mixture was then stirred
  6. extractionthe resulting mixture was extracted with diethyl ether
  7. washThe extract was washed with water, dilute hydrochloric acid
  8. dry with materiala saturated aqueous solution of sodium chloride, successively, dried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-417d9c004e9d4ddb915af227f99c2b35
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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