Hydrogen Peroxide → Ethiprole

HRID 2186117Notes

Reaction equation

HRID 2186117 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]([C:19]#[N:20])[C:3]=1[S:21][CH2:22][CH3:23].S(=O)(=O)(O)[OH:25].OO>CO.C(O)(C)C>[NH2:1][C:2]1[N:6]([C:7]2[C:8]([Cl:18])=[CH:9][C:10]([C:14]([F:17])([F:15])[F:16])=[CH:11][C:12]=2[Cl:13])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[S:21]([CH2:22][CH3:23])=[O:25]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 111117145-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(ethylthio)-1H-pyrazole-3-carbonitrile

Product 1

HCID 9930667EthiproleYield 302.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-ethylthiopyrazole (22.25 g) in methanol was added a solution of sulfuric acid (1.5 g) in isopropanol. Hydrogen peroxide (6.95 g of 30% aqueous solution) was added and the temperature raised to 60° C. After two hours, the reaction was filtered and the solid washed with methanol. The filtrate was washed (water), dried and recrystallized (methanol) to give 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-ethylsulfinylpyrazole (18.4 g), m.p. 173-174° C.

Workup

  1. filtrationthe reaction was filtered
  2. washthe solid washed with methanol
  3. washThe filtrate was washed (water)
  4. customdried
  5. customrecrystallized (methanol)

Sources & evidence

ORD record
ord-c9c12d72fdc84dbdb00867302c707b8d
Source dataset
uspto-grants-2002_06
Patent number
US06403628B1

Reaction notes

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