O-Methylhydroxylamine hydrochloride → HCID 85433387, compound

HRID 2301362Notes

Reaction equation

HRID 2301362 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([CH:19]=O)[C:3]=1[S:21][C:22]([F:25])([F:24])[F:23].Cl.[CH3:27][O:28][NH2:29]>N1C=CC=CC=1>[CH3:27][O:28][N:29]=[CH:19][C:4]1[C:3]([S:21][C:22]([F:25])([F:24])[F:23])=[C:2]([NH2:1])[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:15])([F:17])[F:16])=[CH:9][C:8]=2[Cl:18])[N:5]=1

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 12056606HCID 12056606, compound

Product 1

HCID 85433387HCID 85433387, compoundYield 42.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-trifluoromethylthio-1H-pyrazole-3-carboxaldehyde (0.66 g), methoxyamine hydrochloride (0.2 g) and pyridine was stirred at room temperature for 26 hours. Pyridine was evaporated and the residue dissolved in ethyl acetate/acetonitrile, washed with 1% aqueous HCl, dried (MgSO4) and evaporated. The residue was purified by silica gel column chromatography, eluting with hexane/ethyl acetate, to give 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-trifluoromethylthio-1-H-pyrazole-3-carboxaldehyde-O-methyloxime (0.3 g) as a white solid m.p. 129-131.5° C. Compound 9.

Workup

  1. customPyridine was evaporated
  2. dissolutionthe residue dissolved in ethyl acetate/acetonitrile
  3. washwashed with 1% aqueous HCl
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with hexane/ethyl acetate

Sources & evidence

ORD record
ord-e13dfffeff5f44d48e335fbdff1106a2
Source dataset
uspto-grants-2002_12
Patent number
US06500850B2

Reaction notes

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