m-Chloroperbenzoic acid → HCID 19780318, compound

HRID 2081639Notes

Reaction equation

HRID 2081639 reaction equation
[CH:1]([S:4][C:5]1[S:6][C:7]([CH2:10][NH:11][C:12]([C:14]2[N:18]([CH3:19])[N:17]=[C:16]([CH2:20][CH3:21])[C:15]=2[Cl:22])=[O:13])=[CH:8][N:9]=1)([CH3:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:31])C=1>C(Cl)(Cl)Cl>[CH:1]([S:4]([C:5]1[S:6][C:7]([CH2:10][NH:11][C:12]([C:14]2[N:18]([CH3:19])[N:17]=[C:16]([CH2:20][CH3:21])[C:15]=2[Cl:22])=[O:13])=[CH:8][N:9]=1)=[O:31])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 19780316HCID 19780316, compound

Product 1

HCID 19780318HCID 19780318, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

0.65 g of N[2-(isopropylthio)thiazol-5-ylmethyl]-4-chloro-3-ethyl-1-methylpyrazole-5-carboxamide was dissolved in 20 ml of chloroform, to which was added little by little 0.40 g of metachloroperbenzoic acid, and the mixture was stirred at room temperature overnight. The resultant solution was washed with saturated aqueous sodium hydrogencarbonate, then with saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica-gel chromatography (developing solvent: ethyl acetate/hexane=2/1) to obtain 0.46 g of the titled compound.

Workup

  1. washThe resultant solution was washed with saturated aqueous sodium hydrogencarbonate
  2. dry with materialwith saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe residue was purified by silica-gel chromatography (developing solvent: ethyl acetate/hexane=2/1)

Sources & evidence

ORD record
ord-3e9b45a532d9478c874c3b5761824840
Source dataset
uspto-grants-1993_02
Patent number
US05185354

Reaction notes

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