Methyl iodide → HCID 70982521, compound

HRID 922597Notes

Reaction equation

HRID 922597 reaction equation
[I:1][C:2]1[N:3]=[CH:4][N:5]([CH2:8][C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=2)[C:6]=1[I:7].I[CH3:20]>C(#N)C>[I-:1].[I:7][C:6]1[N:5]([CH2:8][C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=2)[CH2:4][NH+:3]([CH3:20])[C:2]=1[I:1]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 70982117HCID 70982117, compound

Product 1

HCID 70982521HCID 70982521, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4,5-diiodoimidazole (5.0 mmol) and KOH (5.0 mmol) were placed in a round bottom flask with 50 mL THF. The mixture was brought to reflux and stirred 0.5 h until KOH was consumed. 2-bromomethylnapthalene (5.0 mmol) was added and the solution was stirred at reflux for 17 hours. KBr was removed by vacuum filtration and the filtrate was collected. The volatiles were removed by rotary evaporation to give 4,5-diiodo-1-(naphthalen-2-ylmethyl)-1H-imidazole as a off white solid. 4,5-diiodo-1-(naphthalen-2-ylmethyl)-1H-imidazole was dissolved in acetonitrile in a round bottom flask. The solution was brought to reflux and excess iodomethane was added. The reaction was stirred at reflux for overnight after which time it was cooled. The resulting yellow precipitate was collected by filtration and analyzed. 1H NMR (300 MHz, d6-DMSO): δ 3.88 (s), 5.64 (s), 7.47-7.60 (m), 7.89-8.02 (m), 9.57 (s) ppm.

Workup

  1. temperatureto reflux
  2. temperatureat reflux for overnight after which time it
  3. temperaturewas cooled
  4. filtrationThe resulting yellow precipitate was collected by filtration

Sources & evidence

ORD record
ord-da2c8d6ec44c45d19ca9751c0aa369cf
Source dataset
uspto-grants-2016_03
Patent number
US09278951B2

Reaction notes

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