Imidazole → HCID 13457356, compound

HRID 463278Notes

Reaction equation

HRID 463278 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].[O:8]1[CH:10]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:9]1.O>CN(C)C=O>[OH:8][CH:10]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:9][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 181262-HexyloxiraneHCID 24758Sodium hydride

Product 1

HCID 13457356HCID 13457356, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Imidazole (40.8 g) in 100 ml of dimethyformamide at room temperature was treated with sodium hydride (4.8 g of 50% dispersion in mineral oil). Once a solution was obtained, 1,2-epoxyoctane (40 g) was added dropwise at room temperature and the resulting mixture placed in an oil bath and warmed to 70° for 6 hours with stirring. The resulting cooled solution was then added to 600 ml of water and extracted with ether (4×400 ml). The combined extracts were washed twice with concentrated aqueous potassium hydroxide, dried (MgSO4) and concentrated. The resulting ethereal solution was stored at 0° and the resulting precipitate filtered to give 45.93 g of 1-(2-hydroxyoctyl)imidazole, m.p. 44°-45.5° C.

Workup

  1. customOnce a solution was obtained
  2. customthe resulting mixture placed in an oil bath
  3. temperaturewarmed to 70° for 6 hours
  4. temperatureThe resulting cooled solution
  5. extractionextracted with ether (4×400 ml)
  6. washThe combined extracts were washed twice with concentrated aqueous potassium hydroxide
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customwas stored at 0°
  10. filtrationthe resulting precipitate filtered

Sources & evidence

ORD record
ord-d5f5fd1d063d45f5ac38a0ac34d38f8d
Source dataset
uspto-grants-1985_05
Patent number
US04518607

Reaction notes

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