Acetonitrile → 1-(Pyren-2-ylmethyl)-3-(quinolin-2-ylmethyl)-4,5-dichloroimidazolium chloride

HRID 922671Notes

Reaction equation

HRID 922671 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[Cl:7].[OH-].[K+].Br[CH2:11][C:12]1[CH:25]=[C:24]2[C:26]3=[C:27]4[C:17]([CH:18]=[CH:19][CH:20]=[C:21]4[CH:22]=[CH:23]2)=[CH:16][CH:15]=[C:14]3[CH:13]=1.[C:28](#[N:30])[CH3:29]>>[Cl-:1].[CH:13]1[C:14]2[C:26]3=[C:27]4[C:17](=[CH:16][CH:15]=2)[CH:18]=[CH:19][CH:20]=[C:21]4[CH:22]=[CH:23][C:24]3=[CH:25][C:12]=1[CH2:11][N+:3]1[C:2]([Cl:1])=[C:6]([Cl:7])[N:5]([CH2:29][C:28]2[CH:16]=[CH:15][C:14]3[C:13](=[CH:12][CH:25]=[CH:24][CH:26]=3)[N:30]=2)[CH:4]=1

Participants

5

Reactant 4

HCID 6342Acetonitrile2×HCID 14797Potassium Hydroxide2×HCID 1400184,5-DichloroimidazoleHCID 226139302-(Bromomethyl)pyrene

Product 1

HCID 867197061-(Pyren-2-ylmethyl)-3-(quinolin-2-ylmethyl)-4,5-dichloroimidazolium chloride

Procedure

4,5-Dichloroimidazole (0.18 g, 1.33 mmol) and potassium hydroxide (0.08 g, 1.46 mmol) will be dissolved in a minimum volume of acetonitrile and stirred at reflux for 30 min. 2-(Bromomethyl)pyrene (2.95 g, 10.0 mmol) will be added and the mixture will be returned to reflux for 3 h. The mixture will be filtered hot to remove the KBr generated. A solution of 2-(chloromethyl)quinoline will be prepared by combining 2-(chloromethyl)quinolone hydrochloride (2.14 g, 10 mmol) and potassium hydroxide (0.56 g, 10.0 mmol) in acetonitrile and refluxing the mixture for 30 min, and this solution will be added to the filtrate. The combined mixture will be returned to reflux for 6 h. The volatile components will be removed under reduced pressure, and the resulting solid will be washed with water to remove the KCl generated in the neutralization of the quinoline. The remaining solid will be dried and will be the product.

Workup

  1. temperatureat reflux for 30 min
  2. temperatureto reflux for 3 h
  3. filtrationThe mixture will be filtered hot
  4. customto remove the KBr
  5. customA solution of 2-(chloromethyl)quinoline will be prepared
  6. temperaturerefluxing the mixture for 30 min
  7. additionthis solution will be added to the filtrate
  8. temperatureto reflux for 6 h
  9. customThe volatile components will be removed under reduced pressure
  10. washthe resulting solid will be washed with water
  11. customto remove the KCl
  12. customThe remaining solid will be dried

Sources & evidence

ORD record
ord-6d3f9b8447e8491a95c025713515445c
Source dataset
uspto-grants-2016_03
Patent number
US09278951B2

Reaction notes

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