Benzophenone → N-[(2Z)-2-(3,5-dichloro-2-pyridinyl)-2-propoxyiminoethyl]-2-(trifluoromethyl)benzamide

HRID 55989Notes

Reaction equation

HRID 55989 reaction equation
[Cl:1][C:2]1[C:3]([C:9](=[N:24][O:25][CH2:26][CH2:27][CH3:28])[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(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][CH2:26][CH2:27][CH3:28])/[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:21])([F:20])[F:22])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 2

HCID 3102BenzophenoneHCID 118071572N-[2-(3,5-dichloropyridin-2-yl)-2-(propoxyimino)ethyl]-2-(trifluoromethyl)benzamide

Product 1

HCID 141385420N-[(2Z)-2-(3,5-dichloro-2-pyridinyl)-2-propoxyiminoethyl]-2-(trifluoromethyl)benzamideYield 38.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 218 mg of N-[2-(3,5-dichloropyridin-2-yl)-2-(propoxyimino)ethyl]-2-(trifluoromethyl)benzamide in 3 ml of acetonitrile, 5 mg of benzophenone was added, and the mixture 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 purified by silica gel column chromatography using ethyl acetate-hexane (with a gradient of from 25:75 to 35:65) as the eluent to obtain 83 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-425959ff0c95448d97fedec888e192b1
Source dataset
uspto-grants-2016_09
Patent number
US09434684B2

Reaction notes

Loading…