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

HRID 922691

Reaction equation

HRID 922691 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[Cl:7].[OH-].[K+].[Br:10][CH2:11][CH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=1.[Br:23][CH2:24][C:25]1[CH:30]=[C:29]([CH2:31]Br)[CH:28]=[C:27]([CH2:33]Br)[CH:26]=1.[CH2:35]1[CH2:39]O[CH2:37][CH2:36]1>>[Br-:10].[C:29]1([CH2:31][N+:3]2[C:2]([Cl:1])=[C:6]([Cl:7])[N:5]([CH2:11][CH2:12][C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH:14]=3)[CH:4]=2)[CH:30]=[C:25]([CH2:24][N+:3]2[C:2]([Cl:1])=[C:6]([Cl:7])[N:5]([CH2:11][CH2:12][C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH:14]=3)[CH:4]=2)[CH:26]=[C:27]([CH2:33][N+:3]2[C:2]([Cl:1])=[C:6]([Cl:7])[N:5]([CH2:37][CH2:36][C:35]3[CH:39]=[CH:37][C:36]4[C:35](=[CH:36][CH:37]=[CH:39][CH:35]=4)[CH:39]=3)[CH:4]=2)[CH:28]=1.[Br-:23].[Br-:10]

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 1400184,5-DichloroimidazoleHCID 2282702-(2-Bromoethyl)naphthaleneHCID 5302581,3,5-Tris(bromomethyl)benzene

Product 1

HCID 867197443,3',3''-(benzene-1,3,5-triyltris(methylene))tris(4,5-dichloro-1-(2-(naphthalen-2-yl)ethyl)-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. 2-(bromoethyl)naphthalene (5.15 g, 21.90 mmol) was added to the solution and refluxed for 3 h. Solution was filtered while hot to remove the KBr precipitate and the filtrate was returned to reflux. 1,3,5-tris(bromomethyl)benzene (2.61, 7.30 mmol) was added to the solution and refluxed overnight. The volatiles were removed in vacuo and the resulting waxy yellow solid was washed in ethyl ether. A resulting product will be collected and analyzed.

Workup

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

Sources & evidence

ORD record
ord-794997fb1f68414c9ad8d309b34bc089
Source dataset
uspto-grants-2016_03
Patent number
US09278951B2

Linked notes

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