HCID 131736900, compound → N-[(1Z,2S)-1-(3,5-dichloro-2-pyridinyl)-1-ethoxyiminopropan-2-yl]-2-(trifluoromethyl)benzamide

HRID 56027Notes

Reaction equation

HRID 56027 reaction equation
[Cl:1][C:2]1[C:3]([C:9](=[N:25][O:26][CH2:27][CH3:28])[C@@H:10]([NH:12][C:13](=[O:24])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]([F:23])([F:22])[F:21])[CH3:11])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1>C(#N)C>[Cl:1][C:2]1[C:3](/[C:9](=[N:25]\[O:26][CH2:27][CH3:28])/[C@@H:10]([NH:12][C:13](=[O:24])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]([F:22])([F:21])[F:23])[CH3:11])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

3

Reactant 1

HCID 131736900HCID 131736900, compound

Product 1

HCID 118071523N-[(1Z,2S)-1-(3,5-dichloro-2-pyridinyl)-1-ethoxyiminopropan-2-yl]-2-(trifluoromethyl)benzamideYield 96%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

580 mg of (S)—N-[2-(3,5-dichloropyridin-2-yl)-2-ethoxyimino-1-methylethyl]-2-(trifluoromethyl)benzamide was dissolved in 3 ml of acetonitrile, and the solution was irradiated with light for 8 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 557 mg of the desired product as a colorless 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-8415f0d2876d44dbb5644dd355489a56
Source dataset
uspto-grants-2016_09
Patent number
US09434684B2

Reaction notes

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