Water → HCID 18509291, compound

HRID 1356615Notes

Reaction equation

HRID 1356615 reaction equation
[H-].[Na+].[F: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])=[C:6]([N+:21]([O-:23])=[O:22])[CH:5]=1.[CH2:24](I)[CH3:25].O>CN(C=O)C>[CH2:24]([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]([F:3])=[CH:5][C:6]=1[N+:21]([O-:23])=[O:22])[CH3:25]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 18509257HCID 18509257, compound

Product 1

HCID 18509291HCID 18509291, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (60%, 0.05 g (1.25 mmol)) in DMF (2.0 ml), 4′-fluoro-2′-nitro-p-toluenesulfonanilide (0.31 g (1.00 mmol)) was added with stirring at room temperature. To the resulting mixture, after 15 minutes' stirring at room temperature, ethyl iodide (0.30 ml (3.75 mmol)) was added dropwise. After 30 minutes' heating at 100° 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. Diisopropyl ether was added to the residue and the solid separated was filtered and washed to give 0.25 g (74%) 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. temperatureAfter 30 minutes' heating at 100° 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
  9. additionDiisopropyl ether was added to the residue
  10. customthe solid separated
  11. filtrationwas filtered
  12. washwashed

Sources & evidence

ORD record
ord-6b2191311b934bbfabec2ae49f6adf5c
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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