Sodium Iodide → HCID 178468847, compound

HRID 2417646Notes

Reaction equation

HRID 2417646 reaction equation
[C:1]([N:4]1[CH:8]=[CH:7][N:6]=[CH:5]1)(=[O:3])[CH3:2].Cl[CH2:10][CH2:11][CH2:12][C:13]1[CH:23]=[CH:22][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][CH:14]=1.[I-:24].[Na+]>C(#N)C>[I-:24].[C:1]([N+:4]1[CH:8]=[CH:7][N:6]([CH2:10][CH2:11][CH2:12][C:13]2[CH:23]=[CH:22][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][CH:14]=2)[CH:5]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 171741-(1H-Imidazol-1-yl)ethanoneHCID 309153ethyl 4-(3-chloropropyl)benzoate

Product 1

HCID 178468847HCID 178468847, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
140 °C

Procedure

To 10 ml of dry acetonitrile were added 1.1 g of 1-acetylimidazole, 2.26 g of ethyl 4-(3-chloropropyl)benzoate and 1.5 g of sodium iodide, and the mixture was heated in a sealed tube for 18 hours at 140° C. under stirring. After cooling, the reaction mixture was filtrated to remove insoluble materials and the filtrate was concentrated under reduced pressure. To the residue was added an adequate amount of dry diethyl ether and the resulting powder was collected by filtration to obtain 3.99 g of 1-acetyl-3-[3-(4-ethoxycarbonylphenyl)propyl]imidazolium iodide. (pale yellow hygroscopic amorphous).

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture was filtrated
  3. customto remove insoluble materials
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionTo the residue was added an adequate amount of dry diethyl ether
  6. filtrationthe resulting powder was collected by filtration

Sources & evidence

ORD record
ord-dd1d7490e3164ee7b1d76065e6f006b9
Source dataset
uspto-grants-1984_09
Patent number
US04469865

Reaction notes

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