1-Chloro-2,4-Dinitrobenzene → HCID 18509213, compound

HRID 1356684Notes

Reaction equation

HRID 1356684 reaction equation
[Cl:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH3:8])[C:3]=1[S:9]([NH:12][O:13][CH3:14])(=[O:11])=[O:10].[N+:15]([C:18]1[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[CH:21]=[CH:20][C:19]=1Cl)([O-:17])=[O:16].[H-].[Na+].O>CN(C=O)C>[Cl:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH3:8])[C:3]=1[S:9]([N:12]([C:19]1[CH:20]=[CH:21][C:22]([N+:24]([O-:26])=[O:25])=[CH:23][C:18]=1[N+:15]([O-:17])=[O:16])[O:13][CH3:14])(=[O:10])=[O:11]

Participants

6

Reactant 4

HCID 61-Chloro-2,4-DinitrobenzeneHCID 962WaterHCID 24758Sodium hydrideHCID 18509295HCID 18509295, compound

Product 1

HCID 18509213HCID 18509213, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-chloro-1,3-dimethyl-N-methoxy-4-pyrazolesulfonamide (0.48 g (2.00 mmol)) and 2,4-dinitrochlorobenzene (0.49 g (2.42 mmol)) in DMF (3.0 ml), sodium hydride (60%, 0.09 g (2.25 mmol)) was added dropwise under cooling with ice and with stirring and the mixture was 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 ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography with chloroform-hexane (10:1) as eluent to give 0.65 g (87%) of the title compound as pale yellow crystals.

Workup

  1. temperatureunder cooling with ice
  2. stirringthe mixture was stirred
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ea13388336be42d39368b29e931af1b7
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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