Imidazole → 3-(1,3-Dioxolan-2-yl)-1-(1H-imidazol-1-yl)-3-methylbutan-2-one

HRID 1253136Notes

Reaction equation

HRID 1253136 reaction equation
Cl[CH2:2][C:3](=[O:12])[C:4]([CH:7]1[O:11][CH2:10][CH2:9][O:8]1)([CH3:6])[CH3:5].[NH:13]1[CH:17]=[CH:16][N:15]=[CH:14]1>C(#N)C>[N:13]1([CH2:2][C:3](=[O:12])[C:4]([CH:7]2[O:11][CH2:10][CH2:9][O:8]2)([CH3:6])[CH3:5])[CH:17]=[CH:16][N:15]=[CH:14]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 132699801-Chloro-3-(1,3-dioxolan-2-yl)-3-methylbutan-2-one

Product 1

HCID 132952943-(1,3-Dioxolan-2-yl)-1-(1H-imidazol-1-yl)-3-methylbutan-2-oneYield 58.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

106.8 g (0.55 mol) of 1-chloro-3-(dioxolan-2-yl)-3-methyl-butan-2-one and 74.8 g (1.1 mols) of imidazole in 500 ml of acetonitrile are stirred for 15 hours at 65° C. The solvent is distilled off, the residue is taken up in 800 ml of methylene chloride and the solution is extracted with twice 1 liter of water. The methylene chloride phase is dried over sodium sulphate, and the solvent is distilled off. 71.7 g (57.7% of theory) of 1-(imidazol-1-yl)-3-(dioxolan-2-yl)-3-methyl-butan-2-one are obtained (purity according to gas chromatography 95.4%).

Workup

  1. distillationThe solvent is distilled off
  2. extractionthe solution is extracted with twice 1 liter of water
  3. dry with materialThe methylene chloride phase is dried over sodium sulphate
  4. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-991b90b413244a2bb29b83df224bb4fb
Source dataset
uspto-grants-1988_05
Patent number
US04747869

Reaction notes

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