Potassium Iodide → HCID 131735869, compound

HRID 2206872Notes

Reaction equation

HRID 2206872 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[N:10][OH:11])[CH3:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].[I-].[K+]>C(#N)C>[CH2:23]([O:22][C:20](=[O:21])[CH2:19][O:11][N:10]=[C:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[CH3:9])[CH3:24]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7748Ethyl bromoacetateHCID 94971-(4-Fluorophenyl)ethanone oximeHCID 10796Cesium carbonate

Product 1

HCID 131735869HCID 131735869, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 1-(4-fluorophenyl)ethanone oxime (8.00 g) and caesium carbonate (20.4 g) in acetonitrile was stirred at 20° C. for 30 minutes. Then ethyl bromoacetate (12.2 g) and potassium iodide (8.7 g) were added thereto and the mixture was stirred at 82° C. for 3 hours. Then the reaction mixture was filtered. The solvent was removed from the filtrate under reduced pressure. Purification by column chromatography gave ethyl({[1-(4-fluorophenyl)ethylidene]amino}oxy)acetate (8.7 g).

Workup

  1. stirringthe mixture was stirred at 82° C. for 3 hours
  2. filtrationThen the reaction mixture was filtered
  3. customThe solvent was removed from the filtrate under reduced pressure
  4. customPurification by column chromatography

Sources & evidence

ORD record
ord-625bf3f749aa4ef681da9b52d5463b51
Source dataset
uspto-grants-2016_06
Patent number
US09375009B2

Reaction notes

Loading…