Hydrogen Peroxide → HCID 18005394, compound

HRID 989237Notes

Reaction equation

HRID 989237 reaction equation
[OH:1]O.[Cl:3][C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[C:6]([Cl:14])[C:5]=1[N:15]1[C:19]([CH3:20])=[C:18]([S:21][CH3:22])[C:17]([C:23]#[N:24])=[N:16]1.O>CO.CC(O)C.OS(O)(=O)=O>[Cl:3][C:4]1[CH:9]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:7]=[C:6]([Cl:14])[C:5]=1[N:15]1[C:19]([CH3:20])=[C:18]([S:21]([CH3:22])=[O:1])[C:17]([C:23]#[N:24])=[N:16]1

Participants

6

Reactant 3

HCID 784Hydrogen Peroxide2×HCID 962WaterHCID 18005446HCID 18005446, compound

Product 1

HCID 18005394HCID 18005394, compound

Reagents, catalysts & solvents 2

HCID 86584956HCID 86584956, compoundCatalystHCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

30% Hydrogen peroxide (1.82 ml) was added to a stirred solution of 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-methyl-4-methylthio-1H-pyrazole-3-carbonitrile (6.2 g) in methanol, containing i-PrOH/H2SO4 catalyst (5.31 ml) described by Drabowicz, et al (above) at 0-5° C. The mixture was allowed to warm to 20° C. over 17 hours. Additional hydrogen peroxide (5.46 ml) was added in three portions over the next 24 hours, along with the catalyst (5 ml). After stirring for a further 60 hours water was added to give 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-methyl-4-methylsulfinyl-1H-pyrazole-3-carbonitrile (6.72 g) as a yellow oil (91.7% area purity by HPLC) having a retention time of 3.61 minutes on a 25.0 centimeter by 4.6 millimeter SUPELCOSIL LC-18 column, eluting with CH3CN/H2O (3:1) solvent at 1 ml/minute.

Workup

  1. customdescribed by Drabowicz, et al (above) at 0-5° C
  2. additionwas added

Sources & evidence

ORD record
ord-6f3815b8e6ee453d925867e04cd0386e
Source dataset
uspto-grants-2003_10
Patent number
US06638956B2

Reaction notes

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