Imidazole → 1-[2-(2-methyl-1,3-dioxolan-2-yl)propyl]-1H-imidazole

HRID 1583425Notes

Reaction equation

HRID 1583425 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[CH3:6][O-].[Na+].[CH3:9][C:10]1([CH2:15][CH2:16]CBr)[O:14][CH2:13][CH2:12][O:11]1>CN(C)C=O>[CH3:9][C:10]1([CH:15]([CH3:16])[CH2:6][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)[O:11][CH2:12][CH2:13][O:14]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 5600542-(3-Bromopropyl)-2-methyl-1,3-dioxolaneHCID 10942334Sodium Methoxide

Product 1

HCID 202606171-[2-(2-methyl-1,3-dioxolan-2-yl)propyl]-1H-imidazoleYield 47.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 29.0 g of imidazole and 23.1 g of sodium methoxide in 385 ml of dimethylformamide was stirred for 30 minutes and cooled in an ice bath as 85.8 g of 3-(2-methyl-1,3-dioxolan-2-yl)propyl bromide was added dropwise. The resulting mixture was maintained at room temperature for 30 minutes and heated to reflux for 1 hour. The solvent was evaporated in vacuo, the residue diluted with acetone and filtered. The filtrate was concentrated and the residue was distilled to afford 37.9 g (47%) of 1-[2-(2-methyl-1,3-dioxolan-2-yl)propyl]-1H-imidazole as a colorless oil, bp 102°-108° C./0.1 mm.

Workup

  1. additionwas added dropwise
  2. temperatureheated
  3. temperatureto reflux for 1 hour
  4. customThe solvent was evaporated in vacuo
  5. additionthe residue diluted with acetone
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. distillationthe residue was distilled

Sources & evidence

ORD record
ord-a662a8656dc34ca2baa53b5404a660f5
Source dataset
uspto-grants-1985_11
Patent number
US04551460

Reaction notes

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