m-Chloroperbenzoic acid → HCID 14879424, compound

HRID 1885814Notes

Reaction equation

HRID 1885814 reaction equation
[CH2:1]([N:3]([CH2:23][CH3:24])[C:4]([N:6]1[CH:10]=[N:9][C:8]([S:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:13]=2[Cl:22])=[N:7]1)=[O:5])[CH3:2].ClC1C=CC=C(C(OO)=[O:33])C=1>C(Cl)(Cl)Cl>[CH2:23]([N:3]([CH2:1][CH3:2])[C:4]([N:6]1[CH:10]=[N:9][C:8]([S:11]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:20])([F:21])[F:19])=[CH:14][C:13]=2[Cl:22])=[O:33])=[N:7]1)=[O:5])[CH3:24]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 14879254HCID 14879254, compound

Product 1

HCID 14879424HCID 14879424, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1-(Diethylcarbamoyl)-3-(2-chloro-4-trifluoromethylphenylthio)-1,2,4-triazole (3.79 g) is dissolved in chloroform (100 ml). With the temperature held at 10° C. or below with ice water, m-chloro-perbenzoic acid (1.73 g) is added in small portions over a period of 10 minutes. Thereafter, reaction is performed at 10° C. for 2 h, then at room temperature for 10 h. The chloroform solution is washed twice with a 10% aqueous solution of potassium carbonate (100 ml), then washed with water, and dried with magnesium sulfate. When the solvent is distilled off, an oil remains. This is purified by silica gel chromatography (solvent 1:1 mixture of chloroform and n-hexane) to produce the titled compound, 1-(diethylcarbamoyl)-3-(2-chloro-4-trifluoromethylphenylsulfinyl)-1,2,4-triazole (2.7 g) as an oil; yield, 68.4%.

Workup

  1. additionis added in small portions over a period of 10 minutes
  2. customThereafter, reaction
  3. waitat room temperature for 10 h
  4. washThe chloroform solution is washed twice with a 10% aqueous solution of potassium carbonate (100 ml)
  5. washwashed with water
  6. dry with materialdried with magnesium sulfate
  7. distillationWhen the solvent is distilled off
  8. customThis is purified by silica gel chromatography (solvent 1:1 mixture of chloroform and n-hexane)

Sources & evidence

ORD record
ord-fa741fe7e6d84c6993180d2c30a09ae7
Source dataset
uspto-grants-1992_09
Patent number
US05147445

Reaction notes

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