Pentanoic acid, 2-bromo- → 1,3-bis(4-carboxybutyl)-4,5-dichloro-1H-imidazol-3-ium bromide

HRID 922688Notes

Reaction equation

HRID 922688 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[Cl:7].[OH-:8].[K+].[Br:10][CH:11]([CH2:15][CH2:16][CH3:17])[C:12]([OH:14])=[O:13]>C(#N)C>[Br-:10].[C:12]([CH2:11][CH2:15][CH2:16][CH2:17][N:3]1[C:2]([Cl:1])=[C:6]([Cl:7])[N+:5]([CH2:17][CH2:16][CH2:15][CH2:11][C:12]([OH:13])=[O:8])=[CH:4]1)([OH:14])=[O:13]

Participants

5

Reactant 3

HCID 11446Pentanoic acid, 2-bromo-HCID 14797Potassium HydroxideHCID 1400184,5-Dichloroimidazole

Product 1

HCID 867197381,3-bis(4-carboxybutyl)-4,5-dichloro-1H-imidazol-3-ium bromide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4,5-dichloroimidazole (1.00 g, 7.36 mmol) was dissolved in acetonitrile. Potassium hydroxide (0.828 g, 14.72 mmol) was added to the solution and allowed to reflux for 30 min. 2 equivalents of 2-bromopentanoic acid (2.66 g, 14.72 mmol) was added to the solution and refluxed for 5 h. Solution was filtered to remove the KBr precipitate and neutralized with 6M HBr. Volatiles were removed in vacuo and the resulting product will be collected and analyzed.

Workup

  1. temperatureto reflux for 30 min
  2. temperaturerefluxed for 5 h
  3. filtrationSolution was filtered
  4. customto remove the KBr precipitate
  5. customVolatiles were removed in vacuo
  6. customthe resulting product will be collected

Sources & evidence

ORD record
ord-55e0a212372645b1b27a8e3bfd939ff8
Source dataset
uspto-grants-2016_03
Patent number
US09278951B2

Reaction notes

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