Methanol → HCID 86644484, compound

HRID 2404550Notes

Reaction equation

HRID 2404550 reaction equation
C([C:3]1[N:7]([C:8]2[CH:13]=[C:12]([S:14][CH2:15][C:16]([F:19])([F:18])[F:17])[C:11]([CH3:20])=[CH:10][C:9]=2[F:21])[N:6]=[C:5]([O:22][C:23]([F:32])([F:31])[CH:24]([F:30])[O:25][C:26]([F:29])([F:28])[F:27])[CH:4]=1)=O.C([O-])(=O)C.[Na+].[Cl-].[OH:39][NH3+:40].[CH3:41]O>>[F:21][C:9]1[CH:10]=[C:11]([CH3:20])[C:12]([S:14][CH2:15][C:16]([F:19])([F:17])[F:18])=[CH:13][C:8]=1[N:7]1[C:3](=[N:40][OH:39])[C:4](=[CH2:41])[C:5]([O:22][C:23]([F:31])([F:32])[CH:24]([F:30])[O:25][C:26]([F:27])([F:28])[F:29])=[N:6]1

Participants

5

Reactant 4

HCID 887MethanolHCID 21645Hydroxylamine HClHCID 517045Sodium AcetateHCID 86644482HCID 86644482, compound

Product 1

HCID 86644484HCID 86644484, compound

Procedure

Then, 0.43 g of 5-formyl-1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}-3-{1,1,2-trifluoro-2-(trifluoromethoxy)ethoxy}pyrazole was dissolved in 15 mL of methanol, and 110 mg of sodium acetate and 90 mg of hydroxylammonium chloride were added, followed by stirring under reflux with heating for 2 hours. Then, the solvent was distilled off under reduced pressure, extraction with ethyl acetate was carried out, the organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the obtained residue was purified by column chromatography (developing solvent ethyl acetate:hexane=1:3) to obtain 0.29g of 1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}-5-(hydroxyimino)methylene-3-{1,1,2-trifluoro-2-(trifluoromethoxy)ethoxy}pyrazole (1H-NMR (CDCL3/TMS δ (ppm) value) 6: (majar) 2.55 (3H, s), 3.38 (2H, q), 6.05 (1H, dt), 6.54 (1H, s), 7.15 (1H, d), 7.61 (1H, d), 7.71 (1H, brs), 7.83 (1H, d)).

Workup

  1. temperatureunder reflux
  2. temperaturewith heating for 2 hours
  3. distillationThen, the solvent was distilled off under reduced pressure, extraction with ethyl acetate
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customthe obtained residue was purified by column chromatography (developing solvent ethyl acetate:hexane=1:3)

Sources & evidence

ORD record
ord-6b7e5734241c4698893c32f4eb7e2226
Source dataset
uspto-grants-2014_08
Patent number
US08802713B2

Reaction notes

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