Potassium bisulfate → Flupyradifurone

HRID 1192838Notes

Reaction equation

HRID 1192838 reaction equation
S([O-])(O)(=O)=O.[K+].[Cl:7][C:8]1[N:13]=[CH:12][C:11]([CH2:14][N:15]([CH2:25][CH:26]([F:28])[F:27])[C:16]([C:18]2[C:19](=[O:24])[O:20][CH2:21]C=2O)=O)=[CH:10][CH:9]=1>C(#N)CCC>[Cl:7][C:8]1[N:13]=[CH:12][C:11]([CH2:14][N:15]([CH2:25][CH:26]([F:27])[F:28])[C:16]2[CH2:21][O:20][C:19](=[O:24])[CH:18]=2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 516920Potassium bisulfateHCID 86661408N-[(6-chloropyridin-3-yl)methyl]-N-(2,2-difluoroethyl)-4-hydroxy-2-oxo-2,5-dihydrofuran-3-carboxamide

Product 1

HCID 16752772FlupyradifuroneYield 77%

Reagents, catalysts & solvents 1

HCID 8008ButyronitrileSolvent

Procedure

At room temperature, 0.5 g of potassium hydrogensulphate are added to a suspension of 1.7 g of N-[(6-chloropyridin-3-yl)methyl]-N-(2,2-difluoroethyl)-4-hydroxy-2-oxo-2,5-dihydrofuran-3-carboxamide in 50 ml of butyronitrile. The mixture is heated at reflux for 5 hours. It is then cooled to room temperature and washed with 30 ml of water. The solvent is removed in vacuo. This gives 1 g of 4-[[(6-chloropyridin-3-yl)methyl](2,2-difluoroethyl)amino]furan-2(5H)-one (this corresponds to 77% yield).

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 5 hours
  3. washwashed with 30 ml of water
  4. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-68cd70be31744863b251c228f2a37ec0
Source dataset
uspto-grants-2014_03
Patent number
US08680285B2

Reaction notes

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