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

HRID 2083725Notes

Reaction equation

HRID 2083725 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

To α-bromo-p-chloroacetophenone (4.64 g) in acetonitrile (50 ml) was added 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 to the residue water was added. The yellow solid which precipitated 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, m.p. 148°-150°.

Workup

  1. temperaturerefluxed for one hour
  2. customThe solvent was removed under reduced pressure and to the residue water
  3. additionwas added
  4. customThe yellow solid which precipitated
  5. filtrationwas filtered
  6. washwashed with water
  7. customdried
  8. customCrystallisation from ethanol-petroleum ether (60°-80°)

Sources & evidence

ORD record
ord-6696473d5a2144249952bbfe8bb1985b
Source dataset
uspto-grants-1978_04
Patent number
US04086351

Reaction notes

Loading…