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

HRID 922673Notes

Reaction equation

HRID 922673 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>C(#N)C>[Br-:10].[CH:25]1[C:24]2[C:26]3=[C:27]4[C:21](=[CH:22][CH:23]=2)[CH:20]=[CH:19][CH:18]=[C:17]4[CH:16]=[CH:15][C:14]3=[CH:13][C:12]=1[CH2:11][N+:3]1[C:2]([Cl:1])=[C:6]([Cl:7])[N:5]([CH2:11][C:12]2[CH:25]=[C:24]3[C:26]4=[C:27]5[C:17]([CH:18]=[CH:19][CH:20]=[C:21]5[CH:22]=[CH:23]3)=[CH:16][CH:15]=[C:14]4[CH:13]=2)[CH:4]=1

Participants

5

Reactant 3

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

Product 1

HCID 867197101,3-Bis(pyren-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. A second equivalent of 2-(bromomethyl)pyrene 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. additionA second equivalent of 2-(bromomethyl)pyrene will be added to the filtrate
  6. temperatureto reflux for 6 h
  7. customThe volatile components will be removed under reduced pressure
  8. customto yield the product

Sources & evidence

ORD record
ord-6fbbdabb0a7f4ba3bab074049af15f7a
Source dataset
uspto-grants-2016_03
Patent number
US09278951B2

Reaction notes

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