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

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

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.