Sodium Iodide → HCID 67786193, compound

HRID 275280Notes

Reaction equation

HRID 275280 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[I-:10].[Na+].[C:12]([N:15]1[CH:19]=[CH:18][N:17]=[CH:16]1)(=O)[CH3:13]>C(#N)C>[I-:10].[C:4]1([CH2:3][CH2:2][NH+:17]2[CH:18]=[CH:19][N:15]([CH2:12][CH2:13][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH2:16]2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 7666Phenethyl bromideHCID 171741-(1H-Imidazol-1-yl)ethanone

Product 1

HCID 67786193HCID 67786193, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

A solution of (2-bromoethyl)benzene (27.3 ml), sodium iodide (60.0 g), 1-acetylimidazole (22.2 g), and acetonitrile (220 ml) was refluxed 6.5 hrs. under nitrogen. The solution was cooled to 25° C. and the acetonitrile was evaporated. Water and potassium carbonate were added to the oily residue, which was extracted with dichloromethane. Combined extracts were washed with water, dried, filtered, and concentrated to give 1,3-bis(2-phenylethyl)-1H-imidazolium iodide (J, 35.4 g), m.p. 145.5°-147° C. from ethyl acetate.

Workup

  1. customthe acetonitrile was evaporated
  2. additionWater and potassium carbonate were added to the oily residue, which
  3. extractionwas extracted with dichloromethane
  4. washCombined extracts were washed with water
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-da81463fdc1e4df6aaca0d868777b931
Source dataset
uspto-grants-1995_02
Patent number
US05393753

Reaction notes

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