Water → HCID 18509212, compound

HRID 1356620Notes

Reaction equation

HRID 1356620 reaction equation
[H-].[Na+].[Cl: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](Br)[CH:25]=[CH2:26].O>CN(C=O)C>[CH2:26]([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]([Cl:3])=[CH:5][C:6]=1[N+:21]([O-:23])=[O:22])[CH:25]=[CH2:24]

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 3691019HCID 3691019, compound

Product 1

HCID 18509212HCID 18509212, compoundYield 62.2%

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′-chloro-2′-nitro-p-toluenesulfonanilide (0.30 g (0.92 mmol)) was added with stirring at room temperature. To the resulting mixture, after 15 minutes' stirring at room temperature, allyl bromide (0.50 ml (5.78 mmol)) was added dropwise. After being stirred for 30 minutes' at 50° C. and for 15 hours 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. Diisopropyl ether was added to the residue, and the crystals separated was filtered and washed to give 0.21 g (62%) 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 being stirred for 30 minutes' at 50° C.
  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. additionDiisopropyl ether was added to the residue
  9. customthe crystals separated
  10. filtrationwas filtered
  11. washwashed

Sources & evidence

ORD record
ord-37813f662d6c49aa9da6093bfb9cd5e5
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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