Imidazole → HCID 19806280, compound

HRID 1681327Notes

Reaction equation

HRID 1681327 reaction equation
Br[CH:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([O:5][CH3:6])=[O:4].[NH:13]1[CH:17]=[CH:16][N:15]=[CH:14]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[N:13]1([CH:2]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]([O:5][CH3:6])=[O:4])[CH:17]=[CH:16][N:15]=[CH:14]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 137806Benzeneacetic acid, alpha-bromo-, methyl ester

Product 1

HCID 19806280HCID 19806280, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

(RS) Methyl 2-bromo-2-phenylacetate (171.75 g), imidazole (102 g) and potassium carbonate (227.7 g) were stirred in acetone (1.75 liters for 60 hours. After settling, the supernatant was decanted off and the residue washed thoroughly with acetone. The acetone was evaporated under reduced pressure and the residue in ethyl acetate was washed with water and extracted twice with 2M hydrochloric acid. The combined acid extracts, after washing once with ether, were basified with solid potassium carbonate and extracted with toluene containing 10% ethyl acetate. The organic extracts were dried over magnesium sulphate and evaporated under reduced pressure to give the title compound as a yellow oil (132 g, 8i%).

Workup

  1. customthe supernatant was decanted off
  2. washthe residue washed thoroughly with acetone
  3. customThe acetone was evaporated under reduced pressure
  4. washthe residue in ethyl acetate was washed with water
  5. extractionextracted twice with 2M hydrochloric acid
  6. washThe combined acid extracts, after washing once with ether
  7. extractionextracted with toluene containing 10% ethyl acetate
  8. dry with materialThe organic extracts were dried over magnesium sulphate
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b0e4fe49b18647798f035ec99e40beac
Source dataset
uspto-grants-1992_12
Patent number
US05171744

Reaction notes

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