Tetrahydrofuran → 3,3',3''-(benzene-1,3,5-triyltris(methylene))tris(4,5-dichloro-1-(naphthalen-2-ylmethyl)-1H-imidazol-3-ium) bromide

HRID 922624

Reaction equation

HRID 922624 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:17]=[C:16]([CH2:18]Br)[CH:15]=[C:14]([CH2:20]Br)[CH:13]=1.[Br:22][CH2:23][C:24]1[CH:33]=[CH:32][C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=1.[CH2:34]1[CH2:38]O[CH2:36][CH2:35]1>>[Br-:10].[C:16]1([CH2:18][N+:3]2[C:2]([Cl:1])=[C:6]([Cl:7])[N:5]([CH2:38][C:34]3[CH:28]=[CH:27][C:26]4[C:36](=[CH:32][CH:33]=[CH:24][CH:25]=4)[CH:35]=3)[CH:4]=2)[CH:17]=[C:12]([CH2:11][N+:3]2[C:2]([Cl:1])=[C:6]([Cl:7])[N:5]([CH2:23][C:24]3[CH:33]=[CH:32][C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH:25]=3)[CH:4]=2)[CH:13]=[C:14]([CH2:20][N+:3]2[C:2]([Cl:1])=[C:6]([Cl:7])[N:5]([CH2:36][C:35]3[CH:31]=[CH:30][C:29]4[C:38](=[CH:38][CH:34]=[CH:35][CH:36]=4)[CH:34]=3)[CH:4]=2)[CH:15]=1.[Br-:22].[Br-:10]

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 703202-BromomethylnaphthaleneHCID 1400184,5-DichloroimidazoleHCID 5302581,3,5-Tris(bromomethyl)benzene

Product 1

HCID 867196203,3',3''-(benzene-1,3,5-triyltris(methylene))tris(4,5-dichloro-1-(naphthalen-2-ylmethyl)-1H-imidazol-3-ium) bromide

Procedure

4,5-dichloroimidazole (3.00 g, 21.90 mmol) was dissolved in THF and brought to reflux. Potassium hydroxide (2.46 g, 43.80 mmol) was added to the solution and allowed to reflux for 30 min. 1,3,5-tris(bromomethyl)benzene (2.61, 7.30 mmol) was added to the solution and refluxed overnight. Solution was filtered while hot to remove the KBr precipitate and the filtrate returned to reflux. 2-(bromomethyl)naphthalene (4.84 g, 21.90 mmol) was added to the solution and refluxed for 3 h. The volatiles were removed in vacuo and the resulting waxy yellow solid was washed in ethyl ether. A white precipitate was collected and analyzed. 1H NMR (300 MHz, DMSO-d6): δ 4.87, 5.18, 7.32, 7.57, 7.95, 10.30.

Workup

  1. temperatureto reflux
  2. temperatureto reflux for 30 min
  3. temperaturerefluxed overnight
  4. filtrationSolution was filtered while hot
  5. customto remove the KBr precipitate
  6. temperatureto reflux
  7. temperaturerefluxed for 3 h
  8. customThe volatiles were removed in vacuo
  9. washthe resulting waxy yellow solid was washed in ethyl ether
  10. customA white precipitate was collected

Sources & evidence

ORD record
ord-ddf15657a63c49be977fa70256857053
Source dataset
uspto-grants-2016_03
Patent number
US09278951B2

Linked notes

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