Benzophenone → (E)-N-[2-(3,5-dichloropyridin-2-yl)-2-(isopropoxyimino)ethyl]-2-(trifluoromethyl)benzamide

HRID 56013Notes

Reaction equation

HRID 56013 reaction equation
[Cl:1][C:2]1[C:3](/[C:9](=[N:24]/[O:25][CH:26]([CH3:28])[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]([Cl:8])[CH:7]=1.C(C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(#N)C>[Cl:1][C:2]1[C:3](/[C:9](=[N:24]\[O:25][CH:26]([CH3:28])[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]([Cl:8])[CH:7]=1

Participants

4

Reactant 2

HCID 3102BenzophenoneHCID 118071529(Z)-N-[2-(3,5-dichloropyridin-2-yl)-2-(isopropoxyimino)ethyl]-2-(trifluoromethyl)benzamide

Product 1

HCID 91827460(E)-N-[2-(3,5-dichloropyridin-2-yl)-2-(isopropoxyimino)ethyl]-2-(trifluoromethyl)benzamideYield 89.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 258 mg of (E)-N-[2-(3,5-dichloropyridin-2-yl)-2-(isopropoxyimino)ethyl]-2-(trifluoromethyl)benzamide in 4 ml of acetonitrile, 2 mg of benzophenone was added, and the mixture 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 3:7) as the eluent to obtain 231 mg of the desired product as white crystals.

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-22d2eab2f2404b218ff867aad547c1ba
Source dataset
uspto-grants-2016_09
Patent number
US09434684B2

Reaction notes

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