Hydroxylamine HCl → HCID 86644480, compound

HRID 2404548Notes

Reaction equation

HRID 2404548 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([S:9]([CH2:11][C:12]([F:15])([F:14])[F:13])=O)=[CH:4][C:3]=1[N:16]1[C:20](C=O)=[CH:19][C:18]([O:23][CH2:24][C:25]([F:31])([F:30])[C:26]([F:29])([F:28])[F:27])=[N:17]1.[C:32]([O-])(=O)C.[Na+].[Cl-].[OH:38][NH3+:39]>CO>[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([S:9][CH2:11][C:12]([F:13])([F:15])[F:14])=[CH:4][C:3]=1[N:16]1[C:20](=[N:39][OH:38])[C:19](=[CH2:32])[C:18]([O:23][CH2:24][C:25]([F:31])([F:30])[C:26]([F:29])([F:28])[F:27])=[N:17]1

Participants

5

Reactant 3

HCID 21645Hydroxylamine HClHCID 517045Sodium AcetateHCID 86644481HCID 86644481, compound

Product 1

HCID 86644480HCID 86644480, compoundYield 103.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.3 g of 1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulfinyl)phenyl}-5-formyl-3-(2,2,3,3,3-pentafluoropropoxy)pyrazole was dissolved in 10 mL of methanol, and 79mg of sodium acetate and 67 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 0.31 g of 1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}-5-(hydroxyimino)methylene-3-(2,2,3,3,3-pentafluoropropoxy)pyrazole.

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-75ef8fd2710a4077a33d9ec4f32dc4d0
Source dataset
uspto-grants-2014_08
Patent number
US08802713B2

Reaction notes

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