Acetic Acid → N-[5-oxo-1-(2,4,6-trichlorophenyl)-2-pyrazolin-3-yl]acetamide

HRID 67165Notes

Reaction equation

HRID 67165 reaction equation
[OH-].[K+].[CH3:3][C:4]1[O:8][N:7]=[C:6]([CH2:9][C:10]([NH:12][C:13]2[C:18]([Cl:19])=[CH:17][C:16]([Cl:20])=[CH:15][C:14]=2[Cl:21])=[O:11])[N:5]=1.C(O)(=O)C>C(O)C>[C:4]([NH:5][C:6]1[CH2:9][C:10](=[O:11])[N:12]([C:13]2[C:18]([Cl:19])=[CH:17][C:16]([Cl:20])=[CH:15][C:14]=2[Cl:21])[N:7]=1)(=[O:8])[CH3:3].[Cl:19][C:18]1[CH:17]=[C:16]([Cl:20])[CH:15]=[C:14]([Cl:21])[C:13]=1[NH2:12]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 133805632-(5-Methyl-1,2,4-oxadiazol-3-yl)-N-(2,4,6-trichlorophenyl)acetamide

Product 2

HCID 124712,4,6-TrichloroanilineYield 12%HCID 4497701N-[5-oxo-1-(2,4,6-trichlorophenyl)-2-pyrazolin-3-yl]acetamideYield 48%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 10 g of potassium hydroxide in 200 ml of anhydrous ethanol was added 20 g of 2-(5-methyl-1,2,4-oxadiazol-3-yl)-2',4',6'-trichloroacetanilide. The mixture was heated under reflux for 10 hours. After it cooled, the mixture was acidified with 20 ml of acetic acid and concentrated to almost dryness under reduced pressure. The residue was slurried in water, collected, and dried. The crude product was stirred with 200 ml of hexane for 15 min., and the hexane solution was separated in hot ethanol and allowed to crystallize over night. There was obtained 9.6 g (48%) of 3-acetamido-1-(2,4,6-trichlorophenyl)-2-pyrazolin-5-one, mp 234°-235.5° C., and 1.5 g (12%) of 2,4,6-trichloroaniline.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 10 hours
  3. temperatureAfter it cooled
  4. concentrationconcentrated to almost dryness under reduced pressure
  5. customcollected
  6. customdried
  7. customthe hexane solution was separated in hot ethanol
  8. customto crystallize over night

Sources & evidence

ORD record
ord-36431ecad0c84d19b78bf6146b6598b0
Source dataset
uspto-grants-1982_08
Patent number
US04345085

Reaction notes

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