Hydrogen Peroxide → 4-Bromo-2-(p-chlorophenyl)-1-(ethoxymethyl)-5-(trifluoromethyl)pyrrole-3-carboxamide

HRID 274734

Reaction equation

HRID 274734 reaction equation
[Br:1][C:2]1[C:3]([C:22]#[N:23])=[C:4]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[N:5]([CH2:11][O:12][CH2:13][CH3:14])[C:6]=1[C:7]([F:10])([F:9])[F:8].[OH-:24].[Na+].OO>CO.O>[Br:1][C:2]1[C:3]([C:22]([NH2:23])=[O:24])=[C:4]([C:15]2[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=2)[N:5]([CH2:11][O:12][CH2:13][CH3:14])[C:6]=1[C:7]([F:8])([F:10])[F:9]

Participants

6

Reactant 3

HCID 784Hydrogen Peroxide2×HCID 14798Sodium Hydroxide2×HCID 91778Chlorfenapyr

Product 1

HCID 152390884-Bromo-2-(p-chlorophenyl)-1-(ethoxymethyl)-5-(trifluoromethyl)pyrrole-3-carboxamideYield 86.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 4-bromo-2-(p-chlorophenyl)-1-(ethoxymethyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile (4.07 g, 10 mmol), sodium hydroxide (0.8 g, 20 mmol) and 30 wt/wt % hydrogen peroxide solution (7.2 mL, 70 mmol) in methanol is stirred at room temperature for 7 hours, treated with sodium hydroxide solution (0.8 g NaOH in 5 mL of H2O) and 30 wt/wt % hydrogen peroxide solution (7 mL), stirred at room temperature overnight, heated at 40° C. for 8 hours and diluted with water. The aqueous mixture is filtered and the filter cake is washed with water and heptane and dried to give the title product as a white solid (3.7 g) which is identified by 1H and 13C NMR spectral analyses.

Workup

  1. stirringstirred at room temperature overnight
  2. temperatureheated at 40° C. for 8 hours
  3. filtrationThe aqueous mixture is filtered
  4. washthe filter cake is washed with water and heptane
  5. customdried

Sources & evidence

ORD record
ord-d04b3dc3fe4849988063bd7008219655
Source dataset
uspto-grants-1995_02
Patent number
US05389669

Linked notes

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