Potassium Hydroxide → HCID 70982117, compound

HRID 922596Notes

Reaction equation

HRID 922596 reaction equation
[I:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[I:7].[OH-].[K+].Br[CH2:11][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=1>C1COCC1>[I:1][C:2]1[N:3]=[CH:4][N:5]([CH2:11][C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=2)[C:6]=1[I:7]

Participants

5

Reactant 3

HCID 14797Potassium Hydroxide2×HCID 703202-BromomethylnaphthaleneHCID 27733824,5-Diiodo-1H-imidazole

Product 1

HCID 70982117HCID 70982117, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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. customwas consumed
  3. temperatureat reflux for 17 hours
  4. customKBr was removed by vacuum filtration
  5. customthe filtrate was collected
  6. customThe volatiles were removed by rotary evaporation

Sources & evidence

ORD record
ord-8b26ad893a4d4de0a9a4c4c657beb7f1
Source dataset
uspto-grants-2016_03
Patent number
US09278951B2

Reaction notes

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