Imidazole → 1-(Thiophen-2-yl)-1H-imidazole

HRID 1193564Notes

Reaction equation

HRID 1193564 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].[H][H].I[C:11]1[S:12][CH:13]=[CH:14][CH:15]=1>CN(C=O)C.O>[S:12]1[CH:13]=[CH:14][CH:15]=[C:11]1[N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 189212-IodothiopheneHCID 24758Sodium hydrideHCID 178418361HCID 178418361, compound

Product 1

HCID 153803521-(Thiophen-2-yl)-1H-imidazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
150 °C

Procedure

Under nitrogen, solid imidazole (34 g, 0.5 mol) is added cautiously to a slurry of 20.9 g (0.55 mol) 50% NaH dispersion in 500 ml dry DMF. After hydrogen evolution ceases, 115 g (0.55 mol) 2-iodothiophene in 100 ml DMF is added. The reaction is heated at 150° C. for 18 hours. After cooling, the reaction is diluted with 2 liters of water and the product extracted into EtOAc (2×400 ml). After drying, (Na2SO4) the solvent is removed to give crude 1-(2-thienyl)imidazole. The product is purified by vacuum distillation.

Workup

  1. temperatureAfter cooling
  2. extractionthe product extracted into EtOAc (2×400 ml)
  3. customAfter drying
  4. custom(Na2SO4) the solvent is removed

Sources & evidence

ORD record
ord-188ee030ef244968bb931220c924bcf8
Source dataset
uspto-grants-1989_03
Patent number
US04810800

Reaction notes

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