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

HRID 1447021Notes

Reaction equation

HRID 1447021 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.

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-8c537139d20a46cf8fd7efce36c4ca47
Source dataset
uspto-grants-1982_02
Patent number
US04315016

Reaction notes

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