Dichloromethane → 2-(3,5-bis(trifluoromethyl)phenyl-N,2-dimethylpropanamido)-2-chloro-4(o-tolyl)pyridine 1-oxide

HRID 340426Notes

Reaction equation

HRID 340426 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([C:13]([CH3:33])([CH3:32])[C:14]([N:16](C2C=NC(Cl)=CC=2C2C=CC=CC=2C)[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH:36]1[CH:41]=[C:40](Cl)[CH:39]=[C:38]([C:43](OO)=O)[CH:37]=1.[OH-:47].[Na+].[CH2:49]([Cl:51])Cl>>[F:11][C:9]([F:12])([F:10])[C:7]1[CH:6]=[C:5]([C:13]([CH3:32])([CH3:33])[C:14]([N:16]([C:49]2([Cl:51])[CH:4]=[C:5]([C:37]3[CH:36]=[CH:41][CH:40]=[CH:39][C:38]=3[CH3:43])[CH:13]=[CH:14][NH+:16]2[O-:47])[CH3:17])=[O:15])[CH:4]=[C:3]([C:2]([F:1])([F:35])[F:34])[CH:8]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 102295322-(3,5-bis(trifluoromethyl)phenyl)-N-(6-chloro-4-(o-tolyl)pyridin-3-yl)-N,2-dimethylpropanamide

Product 1

HCID 1317320822-(3,5-bis(trifluoromethyl)phenyl-N,2-dimethylpropanamido)-2-chloro-4(o-tolyl)pyridine 1-oxideYield 96.4%

Procedure

To the solution of 2-(3,5-bis(trifluoromethyl)phenyl)-N-(6-chloro-4-(o-tolyl)pyridin-3-yl)-N,2-dimethylpropanamide (5.14 g, 10 mmol) in 60 mL of DCM was added m-CPBA (6.92 g, 40 mmol) at 0° C. under N2 atmosphere. Then the solution was stirred overnight at room temperature. 1 N aq. NaOH solution was added to wash twice for removing the excess m-CPBA. and a side product. The organic phase was washed by brine, dried over Na2SO4, filtered and concentrated to afford 5.11 g of crude 5-(2-(3,5-bis(trifluoromethyl)phenyl-N,2-dimethylpropanamido)-2-chloro-4(o-tolyl)pyridine 1-oxide as a white solid (Yield: 96.4%).

Workup

  1. washto wash twice
  2. customfor removing the excess m-CPBA
  3. washThe organic phase was washed by brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4a17c0612fe946289b1195219fa2beab
Source dataset
uspto-grants-2014_11
Patent number
US08895586B2

Reaction notes

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