Iodoethane → HCID 86740954, compound

HRID 364627Notes

Reaction equation

HRID 364627 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=[N:17][OH:18])[CH2:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1.[H-].[Na+].[CH2:21](I)[CH3:22]>C(COC)OC>[CH2:21]([O:18][N:17]=[C:9]([C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1])[CH2:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)[CH3:22]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 71415949N-[1-(2,4-Dichlorophenyl)-2-(pyridin-3-yl)ethylidene]hydroxylamine

Product 1

HCID 86740954HCID 86740954, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 3 g of 2',4'-dichloro-2-(3-pyridyl)-acetophenone oxime in 25 ml of dimethoxyethane is treated portionwise with 0.51 g of sodium hydride dispersion (55% in oil) and the mixture is stirred for 30 minutes at room temperature. Thereupon, 2.0 g of ethyl iodide are added and the mixture is heated at reflux temperature. After 4 hours, the mixture is poured onto ice and extracted with ethyl acetate. The organic phase is dried over sodium sulfate and concentrated under reduced pressure. The crude product is purified by chromatography on silica gel to yield 2',4'-dichloro-2-(3-pyridyl)-acetophenone O-ethyl oxime as a yellowish oil.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux temperature
  3. waitAfter 4 hours
  4. additionthe mixture is poured onto ice
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic phase is dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-0a49592123134bd585cd2ef112d1106d
Source dataset
uspto-grants-1986_08
Patent number
US04605656

Reaction notes

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