Water → HCID 3591734, compound

HRID 1356614Notes

Reaction equation

HRID 1356614 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:20]=[CH:19][C:7]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:6][C:5]=1[N+:21]([O-:23])=[O:22].S(OC)(O[CH3:28])(=O)=O.O>CN(C=O)C>[CH3:28][N:8]([S:9]([C:12]1[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=1)(=[O:11])=[O:10])[C:7]1[CH:19]=[CH:20][C:4]([CH3:3])=[C:5]([N+:21]([O-:23])=[O:22])[CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 27968454-Methyl-N-(4-methyl-3-nitrophenyl)benzenesulfonamide

Product 1

HCID 3591734HCID 3591734, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (60%, 0.14 g (3.50 mmol)) in DMF (3.0 ml), 4′-methyl-3′-nitro-p-toluenesulfonanilide (1.00 g (3.26 mmol)) was added with stirring at room temperature. To the resulting mixture, after 15 minutes' stirring at room temperature, dimethyl sulfate (0.34 ml (3.56 mmol)) was added dropwise. After one 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. Diethyl ether was added to the residue, and the solid separated was filtered and washed to give 0.79 g (76%) of the title compound as pale yellow crystals.

Workup

  1. additionwas added
  2. stirringTo the resulting mixture, after 15 minutes' stirring at room temperature
  3. stirringAfter one 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. additionDiethyl ether was added to the residue
  9. customthe solid separated
  10. filtrationwas filtered
  11. washwashed

Sources & evidence

ORD record
ord-641338928d4b4508b1d7dd5b96cf1999
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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