Imidazole → HCID 14896351, compound

HRID 1375899Notes

Reaction equation

HRID 1375899 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.Br[CH2:7][CH2:8][CH2:9][CH2:10][Cl:11].[OH-].[Na+].O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CC(C)=O>[Cl:11][CH2:10][CH2:9][CH2:8][CH2:7][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 14798Sodium HydroxideHCID 813641-Bromo-4-chlorobutane

Product 1

HCID 14896351HCID 14896351, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

Imidazole (680 mg), 1-bromo-4-chlorobutane (0.93 ml), tetrabutylammonium iodide (10 mg), and a 3 M aqueous sodium hydroxide solution (1 ml) were dissolved in acetone (10 ml), and the solution was stirred at 50° C. for 18 hr. Water was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed by distillation under the reduced pressure. The residue was purified by chromatography by development with chloroform to give an intermediate (1-(4-chlorobutyl)-1H-imidazole, 756 mg).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was removed by distillation under the reduced pressure
  4. customThe residue was purified by chromatography by development with chloroform

Sources & evidence

ORD record
ord-a272fdc250c7475ba4158eec4a34e2b8
Source dataset
uspto-grants-2007_01
Patent number
US07169789B2

Reaction notes

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