Imidazole → 1-(1H-Imidazol-1-yl)-3,3-dimethylbutan-2-one

HRID 851481Notes

Reaction equation

HRID 851481 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C(=O)([O-])[O-].[K+].[K+].[CH3:12][C:13]([C:16]([CH2:18]Cl)=[O:17])([CH3:15])[CH3:14]>CC(C)=O>[CH3:12][C:13]([CH3:15])([CH3:14])[C:16](=[O:17])[CH2:18][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 835721-Chloropinacolone

Product 1

HCID 127694531-(1H-Imidazol-1-yl)-3,3-dimethylbutan-2-oneYield 89%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

136.2 g (2 moles) of imidazole were added in portions, at room temperature, to 276.4 g (2 moles) of ground potassium carbonate and 269.2 g (2 moles) of α-chloropinacolin in 500 ml of acetone, whereupon the internal temperature rose to the boiling point. The mixture was stirred under reflux for 5 hours and then cooled to room temperature. The reaction mixture was filtered and the filtrate was concentrated by distilling off the solvent in vacuo. The oily residue was distilled. 296 g (89% of theory) of 3,3-dimethyl-1-(imidazol-1-yl)-butan-2-one of melting point ~20° C. were obtained. ##STR45##

Workup

  1. temperatureunder reflux for 5 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. distillationby distilling off the solvent in vacuo
  5. distillationThe oily residue was distilled

Sources & evidence

ORD record
ord-d8456c85a528483093357c63f3ea5855
Source dataset
uspto-grants-1983_05
Patent number
US04385061

Reaction notes

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