Potassium bisulfate → Flupyradifurone

HRID 1192842Notes

Reaction equation

HRID 1192842 reaction equation
S([O-])(O)(=O)=O.[K+].C([O:10][C:11]1[O:12][CH2:13][C:14](=O)[C:15]=1C(OC(C)C)=O)(C)C.[Cl:23][C:24]1[N:29]=[CH:28][C:27]([CH2:30][NH:31][CH2:32][CH:33]([F:35])[F:34])=[CH:26][CH:25]=1>C(#N)CCC>[Cl:23][C:24]1[N:29]=[CH:28][C:27]([CH2:30][N:31]([CH2:32][CH:33]([F:35])[F:34])[C:14]2[CH2:13][O:12][C:11](=[O:10])[CH:15]=2)=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 516920Potassium bisulfateHCID 44604123N-[(6-chloropyridin-3-yl)methyl]-2,2-difluoroethanamineHCID 51050080Isopropyl 2-isopropoxy-4-oxo-4,5-dihydrofuran-3-carboxylate

Product 1

HCID 16752772FlupyradifuroneYield 95%

Reagents, catalysts & solvents 1

HCID 8008ButyronitrileSolvent

Procedure

0.6 g of potassium hydrogensulphate was added at room temperature to a suspension of 1.0 g of isopropyl 2-isopropoxy-4,5-dihydro-4-oxofuran-3-carboxylate and 0.85 g of N-[(6-chloropyridin-3-yl)methyl]-2,2-difluoroethylamine in 15.8 g of butyronitrile. The mixture was heated to reflux for 5 hours. Subsequently, it was cooled to room temperature and washed with 10 ml of water. The solvent was removed under reduced pressure. This gave 1 g of 4-[[(6-chloropyridin-3-yl)methyl](2,2-difluoroethyl)amino]furan-2(5H)-one (this corresponds to 95% yield).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 5 hours
  3. washwashed with 10 ml of water
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-9e72a286b39748e3bfda185ceb428110
Source dataset
uspto-grants-2014_03
Patent number
US08680286B2

Reaction notes

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