Benzophenone → (E)-N-[2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-(cyclopropylmethoxyimino)ethyl]-2-(trifluoromethyl)benzamide

HRID 55996Notes

Reaction equation

HRID 55996 reaction equation
[Cl:1][C:2]1[C:3](/[C:12](=[N:27]/[O:28][CH2:29][CH:30]2[CH2:32][CH2:31]2)/[CH2:13][NH:14][C:15](=[O:26])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]([F:25])([F:24])[F:23])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.C(C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(#N)C>[Cl:1][C:2]1[C:3](/[C:12](=[N:27]\[O:28][CH2:29][CH:30]2[CH2:31][CH2:32]2)/[CH2:13][NH:14][C:15](=[O:26])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]([F:24])([F:25])[F:23])=[N:4][CH:5]=[C:6]([C:8]([F:9])([F:11])[F:10])[CH:7]=1

Participants

4

Reactant 2

HCID 3102BenzophenoneHCID 118071512(Z)-N-[2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-(cyclopropylmethoxyimino)ethyl]-2-(trifluoromethyl)benzamide

Product 1

HCID 118071515(E)-N-[2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-(cyclopropylmethoxyimino)ethyl]-2-(trifluoromethyl)benzamideYield 55.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 85 mg of (E)-N-[2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-(cyclopropylmethoxyimino)ethyl]-2-(trifluoromethyl)benzamide in 3 ml of acetonitrile, 1 mg of benzophenone was added, and the mixture was irradiated with light for 5 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 47 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-b61556a0e6074e42abf315243b20a836
Source dataset
uspto-grants-2016_09
Patent number
US09434684B2

Reaction notes

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