Water → HCID 18509296, compound

HRID 1356613Notes

Reaction equation

HRID 1356613 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:5]=1[NH:6][S:7]([C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)(=[O:9])=[O:8].S(OC)(O[CH3:26])(=O)=O.O>CN(C=O)C>[Cl:3][C:4]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:5]=1[N:6]([CH3:26])[S:7]([C:10]1[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][CH:15]=1)(=[O:8])=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 593188HCID 593188, compound

Product 1

HCID 18509296HCID 18509296, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (60%, 0.07 g (1.75 mmol)) in DMF (2.0 ml), 2′,4′-dichloro-p-toluenesulfonanilide (0.50 g (1.58 mmol)) was added with stirring at room temperature. To the resulting mixture, after 15 minutes' stirring at room temperature, dimethyl sulfate (0.17 ml (1.80 mmol)) was added dropwise. After 15 hours' stirring at room temperature, the reaction mixture was 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 crystals separated were filtered and washed with diisopropyl ether to give 0.38 g (73%) of the title compound.

Workup

  1. additionwas added
  2. stirringTo the resulting mixture, after 15 minutes' stirring at room temperature
  3. stirringAfter 15 hours' stirring at room temperature
  4. extractionextracted with ethyl acetate
  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
  8. customThe crystals separated
  9. filtrationwere filtered
  10. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-89119f7460e34e87a82bc1af090ac1c7
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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