1H-1,2,4-Triazole → Ethanone, 1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-, oxime

HRID 2198421Notes

Reaction equation

HRID 2198421 reaction equation
N1C=NC=N1.C(=O)([O-])[O-].[K+].[K+].[Cl:12][C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[C:20](=O)[CH2:21][N:22]1[CH:26]=[N:25][CH:24]=[N:23]1.Cl.[OH:29][NH3+:30]>C(#N)C.C(O)C.O>[Cl:12][C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[C:20](=[N:30][OH:29])[CH2:21][N:22]1[CH:26]=[N:25][CH:24]=[N:23]1

Participants

8

Reactant 4

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 7393741-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanoneHCID 22029257Hydroxyammonium hydrochloride

Product 1

HCID 787009Ethanone, 1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-, oximeYield 45%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Procedure

269 g (1 mol) of ω-bromo-2,4-dichloroacetophenone were dissolved in 250 ml of acetonitrile. This solution was added dropwise to a suspension, boiling under reflux, of 69 g (1 mol) of 1,2,4-triazole and 150 g of potassium carbonate in 2 liters of acetonitrile. After heating the mixture under reflux for 20 hours, the cooled suspension was filtered, the filtrate was freed from solvent, the residue was taken up in ethyl acetate and the ethyl acetate solution was washed with water, dried over sodium sulphate and freed from solvent. The residue from the ethyl acetate crystallized out when isopropanol was added. After recrystallizing from ligroin/isopropanol, 154 g (60% of theory) of ω-(1,2,4-triazol-1-yl)-2,4-dichloroacetophenone of melting point 117° C. were obtained. ##STR7## 106.8 g (0.44 mol) of 1-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)-ethan-1-one were dissolved in 780 ml of ethanol, 48 g of hydroxylammonium hydrochloride were added and the mixture was heated under reflux for 5 hours. Thereafter, 1,000 ml of water were added, and the reaction mixture was filtered. 51 g (45% of theory) of 1-(2,4-dichlorophenyl)-1-oximino-2-(1,2,4-triazol-1-yl)-ethane of melting point 165°-170° C. were obtained. ##STR8##

Workup

  1. additionThis solution was added dropwise to a suspension
  2. temperatureAfter heating the mixture
  3. temperatureunder reflux for 20 hours
  4. filtrationthe cooled suspension was filtered
  5. washthe ethyl acetate solution was washed with water
  6. dry with materialdried over sodium sulphate
  7. customThe residue from the ethyl acetate crystallized out when isopropanol
  8. additionwas added
  9. customAfter recrystallizing from ligroin/isopropanol, 154 g (60% of theory) of ω-(1,2,4-triazol-1-yl)-2,4-dichloroacetophenone of melting point 117° C.
  10. customwere obtained
  11. temperaturethe mixture was heated
  12. temperatureunder reflux for 5 hours
  13. filtrationthe reaction mixture was filtered

Sources & evidence

ORD record
ord-b60a043661b949cd81be96fca00cc2bb
Source dataset
uspto-grants-1982_11
Patent number
US04357338

Reaction notes

Loading…