Water → HCID 18509284, compound

HRID 1356617Notes

Reaction equation

HRID 1356617 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:21]=[CH:20][C:8]([NH:9][S:10]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)(=[O:12])=[O:11])=[C:7]([N+:22]([O-:24])=[O:23])[CH:6]=1.[CH:25](I)([CH3:27])[CH3:26].O>CN(C=O)C>[CH3:3][O:4][C:5]1[CH:21]=[CH:20][C:8]([N:9]([CH:25]([CH3:27])[CH3:26])[S:10]([C:13]2[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=2)(=[O:12])=[O:11])=[C:7]([N+:22]([O-:24])=[O:23])[CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 225676N-(4-Methoxy-2-nitrophenyl)-4-methylbenzenesulfonamide

Product 1

HCID 18509284HCID 18509284, compoundYield 28.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (60%, 0.10 g (2.50 mmol)) in DMF (2.0 ml), 4′-methoxy-2′-nitro-p-toluenesulfonanilide (0.65 g (2.02 mmol)) was added with stirring at room temperature. To the resulting mixture, after 15 minutes' stirring at room temperature, isopropyl iodide (1.00 g (5.88 mmol)) was added dropwise. After five hours' heating at 130° C. with stirring, 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 residue was subjected to silica gel column chromatography with ethyl acetate-hexane (1:2) as eluent, giving 0.21 g (28.5%) of the title compound as pale brown crystals.

Workup

  1. additionwas added
  2. stirringTo the resulting mixture, after 15 minutes' stirring at room temperature
  3. temperatureAfter five hours' heating at 130° C.
  4. stirringwith stirring
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water and saturated sodium chloride solution
  7. dry with materialsuccessively, dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d8635d41a9b342558a5a34a8b340180e
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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