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Sodium hydride → 2',4'-dichloro-2-(3-pyridyl)acetophenone O-[2-(4-fluorophenoxy)ethyl]oxime

HRID 1681308
Notes
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Reaction equation

HRID 1681308 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:13]=[CH:12][C:7]([O:8][CH2:9][CH2:10]Br)=[CH:6][CH:5]=1.[Cl:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[C:22](=[N:30][OH:31])[CH2:23][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1>CN(C)C=O>[F:3][C:4]1[CH:13]=[CH:12][C:7]([O:8][CH2:9][CH2:10][O:31][N:30]=[C:22]([C:16]2[CH:17]=[CH:18][C:19]([Cl:21])=[CH:20][C:15]=2[Cl:14])[CH2:23][C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)=[CH:6][CH:5]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 20641711-(2-Bromoethoxy)-4-fluorobenzeneHCID 71415949N-[1-(2,4-Dichlorophenyl)-2-(pyridin-3-yl)ethylidene]hydroxylamine

Product 1

HCID 540012232',4'-dichloro-2-(3-pyridyl)acetophenone O-[2-(4-fluorophenoxy)ethyl]oxime

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

0.55 g of sodium hydride dispersion (50% in oil) and then 2.20 g of 2-(4-fluorophenoxy)ethyl bromide are added with stirring to a solution of 2.81 g of 2',4'-dichloro-2-(3-pyridyl)acetophenone oxime in 20 ml of dimethylformamide. The reaction mixture is heated to 100° C. and stirred at this temperature for 1 hour. It is then cooled to room temperature and poured onto ice. The aqueous mixture is extracted with methylene chloride, and the organic phase is washed twice with water, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. After chromatography on silica gel using n-hexane/ethyl acetate (7:3) as the eluent, 2',4'-dichloro-2-(3-pyridyl)acetophenone O-[2-(4-fluorophenoxy)ethyl]oxime is obtained as an E/Z isomer mixture in the form of a slightly yellow oil.

Workup

  1. temperatureIt is then cooled to room temperature
  2. additionpoured onto ice
  3. extractionThe aqueous mixture is extracted with methylene chloride
  4. washthe organic phase is washed twice with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-bec53edc2e6d43508b3515a95325c476
Source dataset
uspto-grants-1992_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05171354

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes