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

HRID 922668Notes

Reaction equation

HRID 922668 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]=[CH:24][C:23]2[C:14](=[CH:15][C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:13]=1.Br[CH2:27][C:28]1[CH:37]=[N:36][C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:29]=1>C(#N)C>[Br-:10].[CH:13]1[C:14]2[C:23](=[CH:22][C:21]3[C:16]([CH:15]=2)=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:24]=[CH:25][C:12]=1[CH2:11][N+:3]1[C:2]([Cl:1])=[C:6]([Cl:7])[N:5]([CH2:27][C:28]2[CH:37]=[N:36][C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[N:29]=2)[CH:4]=1

Participants

6

Reactant 4

HCID 14797Potassium HydroxideHCID 1400184,5-DichloroimidazoleHCID 52877592-(Bromomethyl)quinoxalineHCID 190129612-(Bromomethyl)anthracene

Product 1

HCID 867197001-(Anthracen-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)anthracene (2.71 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-1253f17b3aba4eec92c11351ebe2fd54
Source dataset
uspto-grants-2016_03
Patent number
US09278951B2

Reaction notes

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