m-Chloroperbenzoic acid → HCID 18690749, compound

HRID 1871207Notes

Reaction equation

HRID 1871207 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Cl:12][C:13]1[C:18]([O:19][CH2:20][C:21]#[CH:22])=[CH:17][C:16]([C:23]2[C:27]([CH3:28])=[C:26]([S:29][CH3:30])[N:25]([CH3:31])[N:24]=2)=[C:15]([F:32])[CH:14]=1>ClCCl>[Cl:12][C:13]1[C:18]([O:19][CH2:20][C:21]#[CH:22])=[CH:17][C:16]([C:23]2[C:27]([CH3:28])=[C:26]([S:29]([CH3:30])=[O:9])[N:25]([CH3:31])[N:24]=2)=[C:15]([F:32])[CH:14]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 18690754HCID 18690754, compound

Product 1

HCID 18690749HCID 18690749, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
22 °C

Procedure

A solution of 1.57 g (0.005 mol) of 50-60% 3-chloroperbenzoic acid in 30 ml of dichloromethane is added dropwise at 0-5° C. to a solution of 1.7 g (0.005 mol) of 3-(4-chloro-2-fluoro-5-propargyloxyphenyl)-4-methyl-5-(methylthio)-1-methyl-[1H]-pyrazole (Example P12) in 20 ml of dichloromethane. After being stirred overnight at 22° C., the reaction mixture is washed with a dilute sodium hydrogen carbonate solution, then with water and concentrated by evaporation, and the resulting residue is recrystallised in petroleum ether/diethyl ether. 1.5 g (88.2% of the theoretical yield) of the desired compound are isolated in the form of crystals having a melting point of 93-96° C.

Workup

  1. washthe reaction mixture is washed with a dilute sodium hydrogen carbonate solution
  2. concentrationwith water and concentrated by evaporation
  3. customthe resulting residue is recrystallised in petroleum ether/diethyl ether

Sources & evidence

ORD record
ord-6c4c7e1739144c628ca734c931fa9441
Source dataset
uspto-grants-2000_08
Patent number
US06103667

Reaction notes

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