N-[2-(3,5-dibromopyridin-2-yl)-2-(ethoxyimino)ethyl]-2-(trifluoromethyl)benzamide → N-[(2Z)-2-(3,5-dibromo-2-pyridinyl)-2-ethoxyiminoethyl]-2-(trifluoromethyl)benzamide

HRID 56040Notes

Reaction equation

HRID 56040 reaction equation
[Br:1][C:2]1[C:3]([C:9](=[N:24][O:25][CH2:26][CH3:27])[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]([Br:8])[CH:7]=1>C(#N)C>[Br:1][C:2]1[C:3](/[C:9](=[N:24]\[O:25][CH2:26][CH3:27])/[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:21])([F:20])[F:22])=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1

Participants

3

Reactant 1

HCID 131736905N-[2-(3,5-dibromopyridin-2-yl)-2-(ethoxyimino)ethyl]-2-(trifluoromethyl)benzamide

Product 1

HCID 118071487N-[(2Z)-2-(3,5-dibromo-2-pyridinyl)-2-ethoxyiminoethyl]-2-(trifluoromethyl)benzamideYield 64.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

195 mg of N-[2-(3,5-dibromopyridin-2-yl)-2-(ethoxyimino)ethyl]-2-(trifluoromethyl)benzamide was dissolved in 3 ml of acetonitrile, and the solution was irradiated with light for 12 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 purified by silica gel column chromatography using ethyl acetate-hexane (with a gradient of from 1:9 to 5:5) as the eluent to obtain 125 mg of the desired product as a pale yellow resinous substance.

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated under reduced pressure
  3. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0e297c5b8c9f4d928a2118a8110126f2
Source dataset
uspto-grants-2016_09
Patent number
US09434684B2

Reaction notes

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