Triethylamine → HCID 86644491, compound

HRID 2404555Notes

Reaction equation

HRID 2404555 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([S:9][CH2:10][C:11]([F:14])([F:13])[F:12])=[CH:4][C:3]=1[N:15]1[C:19]([O:20][CH3:21])=[CH:18][C:17]([OH:22])=[N:16]1.C(N(CC)CC)C.[F:30][C:31]([O:35][C:36]([F:39])([F:38])[F:37])=[C:32]([F:34])[F:33].C(OCC)(=O)C>CN(C)C=O>[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([S:9][CH2:10][C:11]([F:14])([F:12])[F:13])=[CH:4][C:3]=1[N:15]1[C:19]([O:20][CH3:21])=[CH:18][C:17]([O:22][C:32]([F:34])([F:33])[CH:31]([F:30])[O:35][C:36]([F:39])([F:38])[F:37])=[N:16]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 14474Perfluoro(methyl vinyl ether)HCID 178493588HCID 178493588, compound

Product 1

HCID 86644491HCID 86644491, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.5 g of 1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}-3-hydroxy-5-methoxypyrazole was dissolved in 30 mL of N,N-dimethylformamide, 40 g of triethylamine was added, and stirring was carried out at 50° C. for 3 hours while trifluoromethyl trifluorovinyl ether was blown. To this solution, ethyl acetate was added, followed by washing with a saturated aqueous solution of citric acid, and then the organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the obtained residue was purified by column chromatography (developing solvent ethyl acetate:hexane=1:4) to obtain 1.1 g of 1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}-5-methoxy-3-{1,1,2-trifluoro-2-(trifluoromethoxy)ethoxy}pyrazole.

Workup

  1. washby washing with a saturated aqueous solution of citric acid
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customthe obtained residue was purified by column chromatography (developing solvent ethyl acetate:hexane=1:4)

Sources & evidence

ORD record
ord-0f2482408edd47a3a3c0515aa477e503
Source dataset
uspto-grants-2014_08
Patent number
US08802713B2

Reaction notes

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