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

HRID 67164Notes

Reaction equation

O1C=NC=N1.N1C(=O)CC=N1.[OH-].[K+].[CH3:14][C:15]1[O:19][N:18]=[C:17]([CH2:20][C:21]([NH:23][C:24]2[C:29]([Cl:30])=[CH:28][C:27]([Cl:31])=[CH:26][C:25]=2[Cl:32])=[O:22])[N:16]=1>C(O)C>[C:15]([NH:16][C:17]1[CH2:20][C:21](=[O:22])[N:23]([C:24]2[C:29]([Cl:30])=[CH:28][C:27]([Cl:31])=[CH:26][C:25]=2[Cl:32])[N:18]=1)(=[O:19])[CH3:14]

Participants

Conditions

Temperature: 80 °C

Procedure

The method of the invention is then used to convert the 1,2,4-oxadiazole to the 2-pyrazolin-5-one. As previously described, the method comprises forming a liquid reaction system of a base catalyst and the 1,2,4-oxadiazole in an organic liquid reaction medium and heating the reaction system to a temperature sufficient to cause the 1,2,4-oxadiazole to be rearranged to the 2-pyrazolin-5-one, e.g., heating a solution of potassium hydroxide and 2-(5-methyl-1,2,4-oxadiazol-3-yl)-2',4',6'-trichloroacetanilide in anhydrous ethanol under reflux at a temperature of 80° C. for 8 to 14 hours to yield 3-acetamido-1-(2,4,6-trichlorophenyl)-2-pyrazolin-5-one, i.e., ##STR7##

Workup

customthe method comprises forming
customa liquid reaction system of a base catalyst
temperatureheating the reaction system to a temperature sufficient

Sources & evidence

ORD record: ord-fb048cce53cd4d838277eec7545f618d
Source dataset: uspto-grants-1982_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04345085

Reaction notes

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