1H-1,2,4-Triazole → HCID 19806285, compound

HRID 1681328Notes

Reaction equation

HRID 1681328 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]=[N:16][CH:15]=[N:14]1.C(=O)([O-])[O-].[K+].[K+]>>[C:7]1([CH:2]([N:13]2[CH:17]=[N:16][CH:15]=[N:14]2)[C:3]([O:5][CH3:6])=[O:4])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 137806Benzeneacetic acid, alpha-bromo-, methyl ester

Product 1

HCID 19806285HCID 19806285, compoundYield 43%

Procedure

A mixture of (RS) methyl 2-bromo-2-phenylacetate (25 g), 1,2,4-triazole (8.28 g) and potassium carbonate (16.5 g) in aetonitrile (200 ml) was refluxed for 3 hours, cooled evaporated under reduced pressure and the residue partitioned between ethyl acetate and 10% potassium carbonate solution. The organic extracts were washed with water, extracted twice with 2M hydrochloric acid and the combined acid extracts, after washing once with ether, were basified with solid potassium carbonate and extracted with ethyl acetate. The organic extracts were dried over magnesium sulphate and evaporated under reduced pressure to give the title compound as a yellow oil (10.2 g, 43%).

Workup

  1. temperaturewas refluxed for 3 hours
  2. temperaturecooled
  3. customevaporated under reduced pressure
  4. customthe residue partitioned between ethyl acetate and 10% potassium carbonate solution
  5. washThe organic extracts were washed with water
  6. extractionextracted twice with 2M hydrochloric acid
  7. washthe combined acid extracts, after washing once with ether
  8. extractionextracted with ethyl acetate
  9. dry with materialThe organic extracts were dried over magnesium sulphate
  10. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-d837e741c1ea4ababe74cebb2df5f8ed
Source dataset
uspto-grants-1992_12
Patent number
US05171744

Reaction notes

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