Ethyl Acetate → Cyclaniliprole

HRID 1641450Notes

Reaction equation

HRID 1641450 reaction equation
[Br:1][C:2]1[CH:6]=[C:5]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[C:17](=[O:24])[NH:18][CH:19]([CH:21]2[CH2:23][CH2:22]2)[CH3:20])=[O:8])[N:4]([C:25]2[C:30]([Cl:31])=[CH:29][CH:28]=[CH:27][N:26]=2)[N:3]=1.C(OCC)(=O)C.[OH-].[Na+].[Br:40]Br>O>[Br:1][C:2]1[CH:6]=[C:5]([C:7]([NH:9][C:10]2[C:11]([C:17]([NH:18][CH:19]([CH:21]3[CH2:23][CH2:22]3)[CH3:20])=[O:24])=[CH:12][C:13]([Cl:16])=[CH:14][C:15]=2[Br:40])=[O:8])[N:4]([C:25]2[C:30]([Cl:31])=[CH:29][CH:28]=[CH:27][N:26]=2)[N:3]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 24408BromineHCID 667361933-bromo-N-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide

Product 1

HCID 24822142CyclaniliproleYield 89.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixed solution comprising 6.0 g of 3-bromo-N-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide and 75 ml of ethyl acetate was cooled with ice, 1.4 g of sodium hydroxide (flakes) was added, and then 2.8 g of bromine was added over a period of 2 hours. After stirring at room temperature for 18 hours, 60 ml of water was added to the reaction liquid, followed by extraction with ethyl acetate. The organic layer was washed with a sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the precipitated crystals were washed with 20 ml of a mixed solution of ethyl acetate and hexane (1:5) and subjected to filtration to obtain 6.2 g of the desired product in the form of white crystals.

Workup

  1. additionwas added
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with a sodium chloride aqueous solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. washthe precipitated crystals were washed with 20 ml of a mixed solution of ethyl acetate and hexane (1:5)
  7. filtrationsubjected to filtration

Sources & evidence

ORD record
ord-3fb7b6c4c3ce434d97a60c4828abc6e2
Source dataset
uspto-grants-2012_02
Patent number
US08115006B2

Reaction notes

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