Triethylamine → HCID 86644497, compound

HRID 2404560Notes

Reaction equation

HRID 2404560 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:25])=[N:8][N:9]([C:11]2[CH:16]=[C:15]([S:17][CH2:18][C:19]([F:22])([F:21])[F:20])[C:14]([CH3:23])=[CH:13][C:12]=2[F:24])[CH:10]=1)=[O:5])[CH3:2].C(N(CC)CC)C.[F:33][C:34]([O:38][C:39]([F:42])([F:41])[F:40])=[C:35]([F:37])[F:36].C(OCC)(=O)C>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:25][C:35]([F:37])([F:36])[CH:34]([F:33])[O:38][C:39]([F:42])([F:41])[F:40])=[N:8][N:9]([C:11]2[CH:16]=[C:15]([S:17][CH2:18][C:19]([F:22])([F:21])[F:20])[C:14]([CH3:23])=[CH:13][C:12]=2[F:24])[CH:10]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 14474Perfluoro(methyl vinyl ether)HCID 178469642HCID 178469642, compound

Product 1

HCID 86644497HCID 86644497, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.20 g of ethyl-1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}-3-hydroxypyrazole-4-carboxylate was dissolved in 40 mL of N,N-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, followed by washing with a saturated aqueous solution of citric acid, and then the organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by column chromatography (developing solvent ethyl acetate:hexane=1:4) to obtain 0.73 g of ethyl-1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}-3-{1,1,2-trifluoro-2-(trifluoromethoxy)ethoxy}pyrazole-4-carboxylate (1H-NMR (CDCL3/TMS δ (ppm) value) δ: 1.36 (3H, t), 2.51 (3H, s), 3.41 (2H, q), 4.34 (2H, q), 6.21 (1H, dt), 7.16 (1H, d), 7.97 (1H, d), 8.38 (1H, d)).

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-b3830b0a97fd4644bb50cb2b277f2887
Source dataset
uspto-grants-2014_08
Patent number
US08802713B2

Reaction notes

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