Potassium Hydroxide → 1-(Pyren-2-ylmethyl)-3-(quinoxalin-2-ylmethyl)-4,5-dichloroimidazolium bromide

HRID 922672Notes

Reaction equation

HRID 922672 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[Cl:7].[OH-].[K+].[Br:10][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.Br[CH2:29][C:30]1[CH:39]=[N:38][C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:31]=1>C(#N)C>[Br-:10].[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:30]2[CH:39]=[N:38][C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[N:31]=2)[CH:4]=1

Participants

6

Reactant 4

HCID 14797Potassium HydroxideHCID 1400184,5-DichloroimidazoleHCID 52877592-(Bromomethyl)quinoxalineHCID 226139302-(Bromomethyl)pyrene

Product 1

HCID 867197081-(Pyren-2-ylmethyl)-3-(quinoxalin-2-ylmethyl)-4,5-dichloroimidazolium bromide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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. 2-(Bromomethyl)quinoxaline (2.23 g, 10.0 mmol) will be added to the filtrate and the mixture will be returned to reflux for 6 h. The volatile components will be removed under reduced pressure to yield 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. temperatureto reflux for 6 h
  6. customThe volatile components will be removed under reduced pressure
  7. customto yield the product

Sources & evidence

ORD record
ord-6487ecafeb1d439d8360aa28a236096e
Source dataset
uspto-grants-2016_03
Patent number
US09278951B2

Reaction notes

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