Sodium hydride → HCID 15457050, compound

HRID 1385926Notes

Reaction equation

HRID 1385926 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[C:11]1[C:12](=[O:21])[NH:13][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:16]=1.[N+:22](C1C=C([N+]([O-])=O)C=CC=1ON)([O-])=O>CN(C=O)C>[NH2:22][N:13]1[C:14]([C:17]([F:20])([F:18])[F:19])=[CH:15][CH:16]=[C:11]([C:5]2[CH:6]=[CH:7][C:8]([Cl:10])=[CH:9][C:4]=2[Cl:3])[C:12]1=[O:21]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 87140O-(2,4-dinitrophenyl)hydroxylamineHCID 15457186HCID 15457186, compound

Product 1

HCID 15457050HCID 15457050, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10 ml of DMF was added to 0.10 g of 60% sodium hydride, and 0.72 g of 3-(2,4-dichlorophenyl)-6-trifluoromethyl-2(1H)-pyridone was added thereto under cooling with ice, followed by stirring further at room temperature for 30 minutes. Then, 0.47 g of 2,4-dinitrophenoxyamine was added thereto at room temperature. Then, the mixture was stirred at 50° C. for 1 hour to complete the reaction. After completion of the reaction, the reaction solution was washed with water and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and then, the solvent was distilled off to obtain a crude product. This crude product was purified by silica gel column chromatography to obtain 0.50 g (yield: 68%) of the desired product. Melting point: 98-100° C.

Workup

  1. additionwas added
  2. temperatureunder cooling with ice
  3. customat room temperature
  4. stirringThen, the mixture was stirred at 50° C. for 1 hour
  5. customthe reaction
  6. customAfter completion of the reaction
  7. washthe reaction solution was washed with water
  8. extractionextracted with ethyl acetate
  9. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  10. distillationthe solvent was distilled off
  11. customto obtain a crude product
  12. customThis crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8781e959f92b4a0da7057d8b38ebf668
Source dataset
uspto-grants-2001_07
Patent number
US06265349B1

Reaction notes

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