Sodium Acetate → HCID 53929848, compound

HRID 1274512Notes

Reaction equation

HRID 1274512 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][CH:23]([CH3:26])[C:24]#[CH:25])=[CH:20][C:19]([NH:27][NH2:28])=[C:18]([F:29])[CH:17]=1>O.C(OCC)C>[Cl:15][C:16]1[C:21]([O:22][CH:23]([CH3:26])[C:24]#[CH:25])=[CH:20][C:19]([N:27]([C:2]2[CH:1]=[CH:18][CH:17]=[CH:16][CH:21]=2)[N:28]=[CH:7][C:8](=[O:9])[C:10]([F:13])([F:12])[F:11])=[C:18]([F:29])[CH:17]=1

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 5505231,1-Dibromo-3,3,3-trifluoroacetoneHCID 54520715HCID 54520715, compound

Product 1

HCID 53929848HCID 53929848, compoundYield 117.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2.870 g of sodium acetate dissolved in 20 ml of water was added 3.139 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 2.000 g of 4-chloro-2-fluoro-5-(1-methyl-2-propynyl)oxyphenylhydrazine dissolved in 10 ml of diethyl ether, and the mixture was stirred at room temperature for 2 hours. After completion of the reaction, 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 2.120 g of 3,3,3-trifluoro-2-oxopropanal 1-(4-chloro-2-fluoro-5-(1-methyl-2-propynyl)oxyphenylphenylhydrazone), compound 3-5.

Workup

  1. waitThe reaction solution was left
  2. stirringthe mixture was stirred at room temperature for 2 hours
  3. customAfter completion of the reaction
  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. concentrationwith 100 ml of saturated aqueous sodium chloride solution, dried with-anhydrous magnesium sulfate, and concentrated
  7. customto give a crude product
  8. customThe crude product was recrystallized from toluene

Sources & evidence

ORD record
ord-f111d100285e4ff3b766ca0989bf5d0e
Source dataset
uspto-grants-2000_12
Patent number
US06156891

Reaction notes

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