N-[2-(3,5-dichloropyridin-2-yl)-2-(2,2,2-trifluoroethoxyimino)ethyl]-2-(trifluoromethyl)benzamide → N-[(2Z)-2-(3,5-dichloro-2-pyridinyl)-2-(2,2,2-trifluoroethoxyimino)ethyl]-2-(trifluoromethyl)benzamide

HRID 56021Notes

Reaction equation

HRID 56021 reaction equation
[Cl:1][C:2]1[C:3]([C:9](=[N:24][O:25][CH2:26][C:27]([F:30])([F:29])[F:28])[CH2:10][NH:11][C:12](=[O:23])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]([F:22])([F:21])[F:20])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1>C(#N)C>[Cl:1][C:2]1[C:3](/[C:9](=[N:24]\[O:25][CH2:26][C:27]([F:30])([F:28])[F:29])/[CH2:10][NH:11][C:12](=[O:23])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]([F:22])([F:21])[F:20])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

3

Reactant 1

HCID 118071540N-[2-(3,5-dichloropyridin-2-yl)-2-(2,2,2-trifluoroethoxyimino)ethyl]-2-(trifluoromethyl)benzamide

Product 1

HCID 91933929N-[(2Z)-2-(3,5-dichloro-2-pyridinyl)-2-(2,2,2-trifluoroethoxyimino)ethyl]-2-(trifluoromethyl)benzamideYield 80.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2.6 g of N-[2-(3,5-dichloropyridin-2-yl)-2-(2,2,2-trifluoroethoxyimino)ethyl]-2-(trifluoromethyl)benzamide was dissolved in 12.0 ml of acetonitrile, and the solution was irradiated with light for 48 hours in a quartz cell (manufactured by Fine, 4 clear windows for spectroscopy) using a 100 W high-pressure mercury lamp (manufactured by USHIO INC., lamp: UM-102, power supply: UM-103B-B). After completion of the reaction, the solvent was evaporated under reduced pressure, and the resulting residue was washed with 20 ml of hexane to obtain 2.1 g of the desired product as white crystals.

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated under reduced pressure
  3. washthe resulting residue was washed with 20 ml of hexane

Sources & evidence

ORD record
ord-7ecb6e4c776c484781cb65ae8e1b25dd
Source dataset
uspto-grants-2016_09
Patent number
US09434684B2

Reaction notes

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