Imidazole → 1-(3-Thienylmethyl)-1H-imidazole

HRID 1193565Notes

Reaction equation

HRID 1193565 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.Br[CH2:7][C:8]1[CH:12]=[CH:11][S:10][CH:9]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[S:10]1[CH:11]=[CH:12][C:8]([CH2:7][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[CH:9]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 5207033-(Bromomethyl)thiophene

Product 1

HCID 212726231-(3-Thienylmethyl)-1H-imidazole

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In a 3 neck, round-bottomed flask reflux a mixture of 11.6 g (0.17 mol) imidazole, 30 g (0.17 mol) 3-bromomethylthiophene, 46 g (0.33 mol) K2CO3 and 400 ml dry acetone. After refluxing for 4 hours filter the reaction mixture and wash the inorganic solids with acetone. Remove the acetone under vacuum and partition the residue betwen H2O/EtOAc. Wash the EtOAc layer several times with H2O, dry (Na2SO4) and concentrate the washed material to obtain a pale yellow oil.

Workup

  1. temperatureIn a 3 neck, round-bottomed flask reflux
  2. temperatureAfter refluxing for 4 hours
  3. filtrationfilter the reaction mixture
  4. washwash the inorganic solids with acetone
  5. customRemove the acetone under vacuum
  6. custompartition the residue betwen H2O/EtOAc
  7. washWash the EtOAc layer several times with H2O
  8. dry with materialdry (Na2SO4)
  9. concentrationconcentrate the washed material
  10. customto obtain a pale yellow oil

Sources & evidence

ORD record
ord-66e5a5fcb9e74908a35b6a0d11ed652a
Source dataset
uspto-grants-1989_03
Patent number
US04810800

Reaction notes

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