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

HRID 922665Notes

Reaction equation

HRID 922665 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:21]=[N:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1>C(#N)C>[Br-:10].[N:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:20]=[CH:21][C:12]=1[CH2:11][N+:3]1[C:2]([Cl:1])=[C:6]([Cl:7])[N:5]([CH2:11][C:12]2[CH:21]=[N:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=2)[CH:4]=1

Participants

5

Reactant 3

HCID 14797Potassium Hydroxide2×HCID 1400184,5-DichloroimidazoleHCID 52877592-(Bromomethyl)quinoxaline2×

Product 1

HCID 867196941,3-Bis(quinoxalin-2-ylmethyl)-4,5-dichloroimidazolium bromide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4,5-dichloroimidazole (1.37 g, 10 mmol) will be dissolved in a minimum amount of acetonitrile and potassium hydroxide (0.62 g, 11 mmol) will be added. The mixture will be stirred at reflux until the potassium hydroxide is consumed, approximately 30 min. 2-(Bromomethyl)quinoxaline (2.23 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 potassium bromide generated. A second addition of 2-(bromomethyl)quinoxaline (2.23 g, 10.0 mmol) will be made to the reaction solution, which will be returned to reflux for 6 h. Removal of the volatile components under reduced pressure should yield the product.

Workup

  1. additionwill be added
  2. customis consumed, approximately 30 min
  3. temperatureto reflux for 3 h
  4. filtrationThe mixture will be filtered hot
  5. customto remove the potassium bromide
  6. temperatureto reflux for 6 h
  7. customRemoval of the volatile components under reduced pressure
  8. customshould yield the product

Sources & evidence

ORD record
ord-054b5819a5b84d47a6bd73a2811a041e
Source dataset
uspto-grants-2016_03
Patent number
US09278951B2

Reaction notes

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