Sodium Iodide → HCID 178472996, compound

HRID 1462927Notes

Reaction equation

HRID 1462927 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH:10]=[CH:9][N:8]=[CH:7]1)=[O:5])[CH3:2].Cl[CH2:12][C:13]1[CH:25]=[CH:24][C:16]([O:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:15][CH:14]=1.[I-:26].[Na+]>C(#N)C>[I-:26].[CH2:1]([O:3][C:4]([N+:6]1[CH:10]=[CH:9][N:8]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([O:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:24][CH:25]=2)[CH:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 87963Ethyl 1H-imidazole-1-carboxylateHCID 4351015(4-Chloromethyl-phenoxy)-acetic acid ethyl ester

Product 1

HCID 178472996HCID 178472996, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.4 g of 1-ethoxycarbonylimidazole, 2.5 g of ethyl 4-chloromethylphenoxyacetate and 1.7 g of sodium iodide were added to 5 ml of dry acetonitrile, and the mixture was stirred at room temperature for 6 hours. After completion of the reaction, 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, the resulting powder was collected by filtration and dried to obtain 4.6 g of 1-ethoxycarbonyl-3-(4-ethoxycarbonylmethoxybenzyl)imidazolium iodide (quantitative yield). Colorless hygroscopic amorphous.

Workup

  1. customAfter completion of the reaction
  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. filtrationthe resulting powder was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-f155f51ea6a94ecc9499bbd71347b6f3
Source dataset
uspto-grants-1984_07
Patent number
US04461905

Reaction notes

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