Potassium bisulfate → Flupyradifurone

HRID 1192840Notes

Reaction equation

HRID 1192840 reaction equation
S([O-])(O)(=O)=O.[K+].C([O:9][C:10]1[O:11][CH2:12][C:13](=O)[C:14]=1C(OCC)=O)C.[Cl:21][C:22]1[N:27]=[CH:26][C:25]([CH2:28][NH:29][CH2:30][CH:31]([F:33])[F:32])=[CH:24][CH:23]=1>C(#N)CCC>[Cl:21][C:22]1[N:27]=[CH:26][C:25]([CH2:28][N:29]([CH2:30][CH:31]([F:33])[F:32])[C:13]2[CH2:12][O:11][C:10](=[O:9])[CH:14]=2)=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 516920Potassium bisulfateHCID 13791062Ethyl 2-ethoxy-4-oxo-4,5-dihydrofuran-3-carboxylateHCID 44604123N-[(6-chloropyridin-3-yl)methyl]-2,2-difluoroethanamine

Product 1

HCID 16752772FlupyradifuroneYield 93%

Reagents, catalysts & solvents 1

HCID 8008ButyronitrileSolvent

Procedure

31.2 g of potassium hydrogensulphate are added at room temperature to a suspension of 46 g of ethyl 2-ethoxy-4,5-dihydro-4-oxofuran-3-carboxylate and 39.3 g of N-[(6-chloropyridin-3-yl)methyl]-2,2-difluoroethylamine in 705 ml of butyronitrile. The mixture was heated to reflux for 5 hours. Subsequently, it was cooled to room temperature and washed with 890 ml of water. The solvent was removed under reduced pressure. This gave 51 g of 4-[[(6-chloropyridin-3-yl)methyl](2,2-difluoroethyl)amino]furan-2(5H)-one (this corresponds to a 93% yield).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 5 hours
  3. washwashed with 890 ml of water
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-6bdbf2d0490d4b26acdd288a56ab33a7
Source dataset
uspto-grants-2014_03
Patent number
US08680286B2

Reaction notes

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