Pyridine → N-Methyl-[5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-1H-pyrazol-3-yl]ethanimine N-oxide

HRID 1738757Notes

Reaction equation

HRID 1738757 reaction equation
[C:1]([C:4]1[C:8]([S:9]([CH3:11])=[O:10])=[C:7]([NH2:12])[N:6]([C:13]2[C:18]([Cl:19])=[CH:17][C:16]([C:20]([F:23])([F:22])[F:21])=[CH:15][C:14]=2[Cl:24])[N:5]=1)(=O)[CH3:2].Cl.[CH3:26][NH:27][OH:28].N1C=CC=CC=1>CO>[CH3:26][N+:27]([O-:28])=[C:1]([C:4]1[C:8]([S:9]([CH3:11])=[O:10])=[C:7]([NH2:12])[N:6]([C:13]2[C:18]([Cl:19])=[CH:17][C:16]([C:20]([F:23])([F:22])[F:21])=[CH:15][C:14]=2[Cl:24])[N:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 77906N-methylhydroxylamine hydrochlorideHCID 11069398Acetoprole

Product 1

HCID 86754584N-Methyl-[5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-1H-pyrazol-3-yl]ethanimine N-oxideYield 36.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 2.0 grams (0.005 mole) of 3-acetyl-5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-1H-pyrazole, 0.83 gram (0.01 mole) of N-methylhydroxylamine hydrochloride, 1.21 ml (0.015 mole) of pyridine and 150 ml of methanol was stirred 68 h at 20° C. The mixture was successively evaporated, washed with CH2Cl2 and water; filtered; washed in hot acetonitrile, acetone, hot methanol; and dried so as to give 0.79 gram of Compound No. 4 (m.p. about 228° C.).

Workup

  1. customThe mixture was successively evaporated
  2. washwashed with CH2Cl2 and water
  3. filtrationfiltered
  4. washwashed in hot acetonitrile
  5. customand dried so as

Sources & evidence

ORD record
ord-e10b30614fcd49fa99619dea30fc9dd8
Source dataset
uspto-grants-1999_10
Patent number
US05965491

Reaction notes

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