Ammonium Chloride → N-[2-(5-bromo-3-chloropyridin-2-yl)-2-(hydroxyimino)ethyl]-2-(trifluoromethyl)benzamide

HRID 56048Notes

Reaction equation

HRID 56048 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([Cl:26])[C:5]([CH:8]([N+:23]([O-])=[O:24])[CH2:9][NH:10][C:11](=[O:22])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]([F:21])([F:20])[F:19])=[N:6][CH:7]=1.CN(C)C=O.O.N([O-])=O.[Na+].[Cl-].[NH4+]>O>[Br:1][C:2]1[CH:3]=[C:4]([Cl:26])[C:5]([C:8](=[N:23][OH:24])[CH2:9][NH:10][C:11](=[O:22])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]([F:20])([F:19])[F:21])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 21962138N,N-Dimethylformamide--water (1/1)HCID 23668193Sodium NitriteHCID 118071621N-[2-(5-bromo-3-chloropyridin-2-yl)-2-nitroethyl]-2-(trifluoromethyl)benzamide

Product 1

HCID 136987062N-[2-(5-bromo-3-chloropyridin-2-yl)-2-(hydroxyimino)ethyl]-2-(trifluoromethyl)benzamideYield 53.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To 6.0 g of N-[2-(5-bromo-3-chloropyridin-2-yl)-2-nitroethyl]-2-(trifluoromethyl)benzamide in 65 ml of a mixture of N,N-dimethylformamide-water (7:1), 6.4 g of sodium nitrite was added, and the mixture was stirred at 60° C. for 18 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, poured into 100 ml of water, mixed with 20 ml of saturated aqueous ammonium chloride and extracted with ethyl acetate (100 ml×2). The resulting organic layers were combined, washed with water (50 ml×1) and dried over saturated aqueous sodium chloride and then anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography using ethyl acetate-hexane (with a gradient of from 2:8 to 6:4) as the eluent to obtain 3.1 g of the desired product as a pale yellow resinous substance.

Workup

  1. customAfter completion of the reaction
  2. temperatureto cool to room temperature
  3. extractionextracted with ethyl acetate (100 ml×2)
  4. washwashed with water (50 ml×1)
  5. dry with materialdried over saturated aqueous sodium chloride
  6. customanhydrous sodium sulfate, and the solvent was evaporated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8d0aedefcb0b48a99f222944e7af9fb5
Source dataset
uspto-grants-2016_09
Patent number
US09434684B2

Reaction notes

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