Propanedioyl dichloride → HCID 68484704, compound

HRID 2404573Notes

Reaction equation

HRID 2404573 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([S:9][CH2:10][C:11]([F:14])([F:13])[F:12])=[CH:4][C:3]=1[NH:15][NH:16][C:17](=[O:19])[CH3:18].[C:20](Cl)(=[O:25])[CH2:21][C:22](Cl)=[O:23]>O1CCCC1>[C:17]([N:16]1[C:22](=[O:23])[CH2:21][C:20](=[O:25])[N:15]1[C:3]1[CH:4]=[C:5]([S:9][CH2:10][C:11]([F:13])([F:14])[F:12])[C:6]([CH3:8])=[CH:7][C:2]=1[F:1])(=[O:19])[CH3:18]

Participants

4

Reactant 2

HCID 74269Propanedioyl dichlorideHCID 68482693HCID 68482693, compound

Product 1

HCID 68484704HCID 68484704, compoundYield 70.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.0 g of N′-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}acetohydrazide was dissolved in 100 mL of tetrahydrofuran, 0.95 g of malonyl chloride was added under cooling with ice, stirring was carried out under cooling with ice for one hour, and then stirring was carried out under reflux with heating for 5 hours. Then, the solvent was distilled off under reduced pressure, and the obtained crystals were washed with isopropyl ether to obtain 1.74 g of 1-acetyl-2-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}pyrazolidine-3,5-dione.

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice for one hour
  3. stirringstirring
  4. temperatureunder reflux
  5. temperaturewith heating for 5 hours
  6. distillationThen, the solvent was distilled off under reduced pressure
  7. washthe obtained crystals were washed with isopropyl ether

Sources & evidence

ORD record
ord-d7b47c17d79d417bb04bc249d14ac847
Source dataset
uspto-grants-2014_08
Patent number
US08802713B2

Reaction notes

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