Triethylamine → HCID 86644435, compound

HRID 2404511Notes

Reaction equation

HRID 2404511 reaction equation
[C:1]([NH:4][C:5]1[N:9]([C:10]2[CH:15]=[C:14]([S:16][CH2:17][C:18]([F:21])([F:20])[F:19])[C:13]([CH3:22])=[CH:12][C:11]=2[F:23])[N:8]=[C:7]([OH:24])[CH:6]=1)(=[O:3])[CH3:2].C(N(CC)CC)C.[F:32][C:33]([O:37][C:38]([F:41])([F:40])[F:39])=[C:34]([F:36])[F:35].C(OCC)(=O)C>CN(C)C=O>[C:1]([NH:4][C:5]1[N:9]([C:10]2[CH:15]=[C:14]([S:16][CH2:17][C:18]([F:19])([F:20])[F:21])[C:13]([CH3:22])=[CH:12][C:11]=2[F:23])[N:8]=[C:7]([O:24][C:34]([F:36])([F:35])[CH:33]([F:32])[O:37][C:38]([F:41])([F:40])[F:39])[CH:6]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 14474Perfluoro(methyl vinyl ether)HCID 178474353HCID 178474353, compound

Product 1

HCID 86644435HCID 86644435, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.0 g of 5-acetylamino-1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}-3-hydroxypyrazole was dissolved in 40 mL of dimethylformamide, 25 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, the solution was washed with a saturated aqueous solution of citric acid, 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 1.71 g of 5-acetylamino-1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}-3-{1,1,2-trifluoro-2-(trifluoromethoxy)ethoxy}pyrazole.

Workup

  1. washthe solution was washed 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-f2cae7d38daf4deca495a7ea08682278
Source dataset
uspto-grants-2014_08
Patent number
US08802713B2

Reaction notes

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