m-Chloroperbenzoic acid → N-[2-Bromo-4-(1-bromo-1,1,2,3,3,3-hexafluoropropan-2-yl)-6-(difluoromethoxy)phenyl]-quinoline-6-carboxamide-1-oxide

HRID 70811Notes

Reaction equation

HRID 70811 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:17])([C:13]([F:16])([F:15])[F:14])[C:9]([Br:12])([F:11])[F:10])[CH:5]=[C:4]([O:18][CH:19]([F:21])[F:20])[C:3]=1[NH:22][C:23]([C:25]1[CH:26]=[C:27]2[C:32](=[CH:33][CH:34]=1)[N:31]=[CH:30][CH:29]=[CH:28]2)=[O:24].ClC1C=CC=C(C(OO)=[O:43])C=1>ClCCl>[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:17])([C:13]([F:15])([F:14])[F:16])[C:9]([Br:12])([F:10])[F:11])[CH:5]=[C:4]([O:18][CH:19]([F:20])[F:21])[C:3]=1[NH:22][C:23]([C:25]1[CH:26]=[C:27]2[C:32](=[CH:33][CH:34]=1)[N+:31]([O-:43])=[CH:30][CH:29]=[CH:28]2)=[O:24]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86672969N-[2-Bromo-4-(1-bromo-1,1,2,3,3,3-hexafluoropropan-2-yl)-6-(difluoromethoxy)phenyl]-quinoline-6-carboxamide

Product 1

HCID 86672968N-[2-Bromo-4-(1-bromo-1,1,2,3,3,3-hexafluoropropan-2-yl)-6-(difluoromethoxy)phenyl]-quinoline-6-carboxamide-1-oxideYield 108.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-[2-Bromo-4-(1-bromo-1,1,2,3,3,3-hexafluoropropan-2-yl)-6-(difluoromethoxy)phenyl]-quinoline-6-carboxamide (0.73 g) was dissolved in dichloromethane (50 ml), added with 3-chloroperbenzoic acid (purity 70%, 0.48 g), and sited at room temperature for S hours. The solvent was distilled off under the reduced pressure and the residue was dissolved in ethyl acetate, Sodium hydrocarbonate solution and potassium carbonate were added thereto. After extracting the mixture twice with ethyl acetate, the organic phases were combined and washed with water, and dried over anhydrous magnesium sulfate. The drying agent (anhydrous magnesium sulfate) was filtered off and the solvent was removed by distillation under the 1.5 reduced pressure to obtain N-[2-bromo-4-(1-bromo-1,1,2,3,3,3-hexafluoropropan-2-yl)-6-(difluoromethoxy)phenyl]quinoline-6-carboxamide-1-oxide (0.81 g, 98%).

Workup

  1. customsited at room temperature for S hours
  2. distillationThe solvent was distilled off under the reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. additionSodium hydrocarbonate solution and potassium carbonate were added
  5. extractionAfter extracting the mixture twice with ethyl acetate
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationThe drying agent (anhydrous magnesium sulfate) was filtered off
  9. customthe solvent was removed by distillation under the 1.5 reduced pressure

Sources & evidence

ORD record
ord-49fef30d9315451796e4194dd8f8f7a7
Source dataset
uspto-grants-2014_09
Patent number
US08822691B2

Reaction notes

Loading…