Water → HCID 18509300, compound

HRID 1356631Notes

Reaction equation

HRID 1356631 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:11]=[CH:10][C:7]([NH:8][CH3:9])=[C:6]([N+:12]([O-:14])=[O:13])[CH:5]=1.[Cl:15][C:16]1[S:20][C:19]([S:21](Cl)(=[O:23])=[O:22])=[CH:18][CH:17]=1.O>CN(C=O)C>[Cl:3][C:4]1[CH:11]=[CH:10][C:7]([N:8]([CH3:9])[S:21]([C:19]2[S:20][C:16]([Cl:15])=[CH:17][CH:18]=2)(=[O:23])=[O:22])=[C:6]([N+:12]([O-:14])=[O:13])[CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27339255-Chlorothiophene-2-sulfonyl chlorideHCID 27368364-chloro-N-methyl-2-nitroaniline

Product 1

HCID 18509300HCID 18509300, compoundYield 16.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (60%, 0.15 g (3.75 mmol)) in DMF (5.0 ml), 4-chloro-N-methyl-2-nitroaniline (0.34 g (1.82 mmol)) was added with stirring at room temperature. To the resulting mixture, after 30 minutes' stirring at room temperature, 5-chloro-2-thiophenesulfonyl chloride (0.67 g (3.11 mmol)) was added. The reaction mixture was stirred at room temperature for 24 hours and then poured into water and extracted with chloroform. 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 then subjected to silica gel column chromatography with acetone-hexane (1:4) as eluent, to give 0.11 g (16%) of the title compound as pale yellow crystals.

Workup

  1. additionwas added
  2. stirringTo the resulting mixture, after 30 minutes' stirring at room temperature
  3. stirringThe reaction mixture was stirred at room temperature for 24 hours
  4. extractionextracted with chloroform
  5. washThe extract was washed with water and saturated sodium chloride solution
  6. dry with materialsuccessively, dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9c87f0aad81c4501a0e9f96a9738e686
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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