Sodium Acetate → HCID 54145894, compound

HRID 2271239Notes

Reaction equation

HRID 2271239 reaction equation
[C:1]([O-])(=O)[CH3:2].[Na+].Br[CH:7](Br)[C:8]([C:10]([F:13])([F:12])[F:11])=[O:9].[Cl:15][C:16]1[C:21]([O:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:20][C:19]([NH:29][NH2:30])=[C:18]([F:31])[CH:17]=1>O.C(OCC)C>[Cl:15][C:16]1[C:21]([O:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:20][C:19]([N:29]([C:2]2[CH:1]=[CH:18][CH:17]=[CH:16][CH:21]=2)[N:30]=[CH:7][C:8](=[O:9])[C:10]([F:13])([F:12])[F:11])=[C:18]([F:31])[CH:17]=1

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 5505231,1-Dibromo-3,3,3-trifluoroacetoneHCID 54270511HCID 54270511, compound

Product 1

HCID 54145894HCID 54145894, compoundYield 135.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1.249 g of sodium acetate dissolved in 10 ml of water was added 1.366 g of 1,1-dibromo-3,3,3-trifluoroacetone, and the mixture was stirred at 80° C. for 30 minutes. The reaction solution was left cooling to room temperature, to which a solution of 1.00 g of 4-chloro-2-fluoro-5-(ethoxycarbonyl)methoxyphenylhydrazine dissolved in 10 ml of diethyl ether was added, and the mixture was stirred at room temperature for 2 hours. The reaction solution was extracted with 100 ml of ethyl acetate. The organic layer was washed with 100 ml of saturated aqueous sodium bicarbonate solution and then with 100 ml of saturated aqueous sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated to give a crude product. The crude product was recrystallized from toluene to give 1.151 g of 3,3,3-trifluoro-2-oxopropanal 1-(4-chloro-2-fluoro-5-(ethoxycarbonyl)methoxyphenylphenylhydrazone), compound 3-8.

Workup

  1. waitThe reaction solution was left
  2. additionwas added
  3. stirringthe mixture was stirred at room temperature for 2 hours
  4. extractionThe reaction solution was extracted with 100 ml of ethyl acetate
  5. washThe organic layer was washed with 100 ml of saturated aqueous sodium bicarbonate solution
  6. dry with materialwith 100 ml of saturated aqueous sodium chloride solution, dried with anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customto give a crude product
  9. customThe crude product was recrystallized from toluene

Sources & evidence

ORD record
ord-2dc71d696abc4013950939115a22c62b
Source dataset
uspto-grants-2001_12
Patent number
US06333413B1

Reaction notes

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