Sodium Iodide → HCID 178469086, compound

HRID 1462926Notes

Reaction equation

HRID 1462926 reaction equation
[C:1]([N:4]1[CH:8]=[CH:7][N:6]=[CH:5]1)(=[O:3])[CH3:2].Br[CH2:10][CH2:11][O: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][O: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 12708668Ethyl 4-(2-bromoethoxy)benzoate

Product 1

HCID 178469086HCID 178469086, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

2.2 g of 1-acetylimidazole, 5.5 g of ethyl 4-(2-bromoethoxy)benzoate, and 3.0 g of sodium iodide were added to 10 ml of dry acetonitrile, and the mixture was heated in a sealed tube under nitrogen atmosphere at 100° C. for 6 hours. After the reaction mixture was cooled, the insoluble materials were filtered off and the filtrate was concentrated under reduced pressure. The residue was triturated with an adequate amount of dry diethyl ether and the r resulting powder was collected by filtration and dried to obtain 6.2 g of 1-acetyl-3-[2-(4-ethoxycarbonylphenoxy)-ethyl]imidazolium iodide (72% yield). Colorless hygroscopic amorphous.

Workup

  1. temperatureAfter the reaction mixture was cooled
  2. filtrationthe insoluble materials were filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was triturated with an adequate amount of dry diethyl ether
  5. customthe r resulting powder
  6. filtrationwas collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-a666325953a347c78ee557b4a8105501
Source dataset
uspto-grants-1984_07
Patent number
US04461905

Reaction notes

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