Triethylamine → 1-(4-Chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-one

HRID 1074893Notes

Reaction equation

HRID 1074893 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1)=[O:4].[NH:12]1[CH:16]=[N:15][CH:14]=[N:13]1.C(N(CC)CC)C>C(#N)C>[N:12]1([CH2:2][C:3]([C:5]2[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=2)=[O:4])[CH:16]=[N:15][CH:14]=[N:13]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 92571H-1,2,4-TriazoleHCID 68303p-Chlorophenacyl bromide

Product 1

HCID 7164721-(4-Chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

α-Bromo-p-chloroacetophenone (4.64 g) in acetonitrile (50 ml) was treated with 1,2,4-triazole (1.4 g) followed by triethylamine (2 g). The mixture was stirred at room temperature for two hours and refluxed for one hour. The solvent was removed under reduced pressure and the residue was treated with water to give a yellow solid which was filtered, washed with water and dried. Crystallisation from ethanol-petroleum ether (60°-80°) gave α-1,2,4-triazol-1-yl-p-chloroacetophenone as cream coloured plates. Analysis:

Workup

  1. temperaturerefluxed for one hour
  2. customThe solvent was removed under reduced pressure
  3. additionthe residue was treated with water
  4. customto give a yellow solid which
  5. filtrationwas filtered
  6. washwashed with water
  7. customdried
  8. customCrystallisation from ethanol-petroleum ether (60°-80°)

Sources & evidence

ORD record
ord-74c7507cfce14e82975f0c9c6e51dad1
Source dataset
uspto-grants-1983_07
Patent number
US04394380

Reaction notes

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