Ethanol → Ethyl 2-bromo-3-(2-butynyl)-5-cyano-3H-imidazole-4-carboxylate

HRID 501390

Reaction equation

HRID 501390 reaction equation
S(=O)(=O)(O)O.[CH2:6](O)[CH3:7].[Br:9][C:10]1[NH:11][C:12]([C:17]#[N:18])=[C:13]([C:15]#N)[N:14]=1.[C:19]([O:22][CH2:23][CH3:24])(=[O:21])[CH3:20]>O>[Br:9][C:10]1[N:14]([CH2:13][C:15]#[C:6][CH3:7])[C:20]([C:19]([O:22][CH2:23][CH3:24])=[O:21])=[C:12]([C:17]#[N:18])[N:11]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 27791482-bromo-1H-imidazole-4,5-dicarbonitrile

Product 1

HCID 23070799Ethyl 2-bromo-3-(2-butynyl)-5-cyano-3H-imidazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4.56 ml of sulfuric acid was added to 170 ml of ethanol containing 16.80 g of 2-bromo-1H-imidazole-4,5-dicarbonitrile [CAS No. 50847-09-1], and the mixture was heated under reflux for 48 hours. The solution was cooled, and then 500 ml of ethyl acetate and 200 ml of water were added thereto. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was dissolved in N,N-dimethylformamide, and 14.1 g of potassium carbonate and 8.6 ml of 2-butynyl bromide were added thereto. The mixture was stirred at room temperature for 18 hours. 500 ml of ethyl acetate was added to the solution, and the mixture was washed three times with 300 ml of water, and then with 300 ml of a saturated sodium chloride solution. Then, the solution was dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography. Thus, 4.09 g of the title compound was obtained from the fraction eluted with hexane-ethyl acetate (9:1).

Workup

  1. temperature50847-09-1], and the mixture was heated
  2. temperatureunder reflux for 48 hours
  3. temperatureThe solution was cooled
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue was dissolved in N,N-dimethylformamide
  8. addition14.1 g of potassium carbonate and 8.6 ml of 2-butynyl bromide were added
  9. addition500 ml of ethyl acetate was added to the solution
  10. washthe mixture was washed three times with 300 ml of water
  11. dry with materialThen, the solution was dried over anhydrous magnesium sulfate
  12. filtrationfiltered
  13. concentrationThe filtrate was concentrated under reduced pressure
  14. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ae898081371343318d97305860d4dc5d
Source dataset
uspto-grants-2010_08
Patent number
US07772226B2

Linked notes

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