Water → Flupyradifurone

HRID 2390988Notes

Reaction equation

HRID 2390988 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH:9][CH2:10][CH:11]([F:13])[F:12])=[CH:4][CH:3]=1.S([O-])(O)(=O)=[O:15].[K+].[OH2:20].ClCCl.[C:24](#N)[CH2:25][CH2:26][CH3:27]>>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]([CH2:10][CH:11]([F:13])[F:12])[C:26]2[CH2:27][O:20][C:24](=[O:15])[CH:25]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6344DichloromethaneHCID 8008ButyronitrileHCID 516920Potassium bisulfateHCID 44604123N-[(6-chloropyridin-3-yl)methyl]-2,2-difluoroethanamine

Product 1

HCID 16752772FlupyradifuroneYield 92%

Conditions

Temperature
92.5 °C

Procedure

To a suspension of 10.4 g of potassium 4-(ethoxycarbonyl)-5-oxo-2,5-dihydrofuran-3-oxide and 7.5 g of N-[(6-chloropyridin-3-yl)methyl]-2,2-difluoroethylamine in 68 ml of butyronitrile are added, at room temperature, 11.5 g of potassium hydrogensulphate. The mixture is stirred at a temperature of 90 to 95° C. for 3 hours. Subsequently, the mixture is cooled to room temperature, 120 ml of water and 120 ml of dichloromethane are added, the organic phase is removed and the aqueous phase is extracted twice with 120 ml each time of methylene chloride. The combined organic phases are concentrated to dryness. 11.4 g of 4[[(6-chloropyridin-3-yl)methyl](2,2-difluoroethyl)amino]furan-2(5H)-one are obtained in a purity of 84% (this corresponds to 92% yield).

Workup

  1. additionare added, at room temperature
  2. temperatureSubsequently, the mixture is cooled to room temperature
  3. customthe organic phase is removed
  4. extractionthe aqueous phase is extracted twice with 120 ml each time of methylene chloride
  5. concentrationThe combined organic phases are concentrated to dryness

Sources & evidence

ORD record
ord-e52ed903c29b4237bae5f5235977804e
Source dataset
uspto-grants-2012_09
Patent number
US08273904B2

Reaction notes

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