Potassium Hydroxide → HCID 178516434, compound

HRID 67167Notes

Reaction equation

HRID 67167 reaction equation
[OH-].[K+].[N+](C1C=CC(O[CH2:11][C:12]2O[N:15]=[C:14]([CH2:17][C:18]([NH:20][C:21]3[C:26]([Cl:27])=[CH:25][C:24]([Cl:28])=[CH:23][C:22]=3[Cl:29])=[O:19])[N:13]=2)=CC=1)([O-])=O.[N+:32]([C:35]1[CH:60]=CC(OCC(NC2CC(=O)N(C3C(Cl)=CC(Cl)=CC=3Cl)N=2)=O)=[CH:37][CH:36]=1)([O-:34])=[O:33]>CO>[N+:32]([C:35]1[CH:60]=[CH:11][C:12]([NH:13][C:14]2[CH2:17][C:18](=[O:19])[N:20]([C:21]3[C:22]([Cl:29])=[CH:23][C:24]([Cl:28])=[CH:25][C:26]=3[Cl:27])[N:15]=2)=[CH:37][CH:36]=1)([O-:34])=[O:33]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 13380572HCID 13380572, compoundHCID 133805733-[(p-Nitro-phenoxy)acetamido]-1-(2,4,6-trichlorophenyl)-2-pyrazolin-5-one

Product 1

HCID 178516434HCID 178516434, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5 g of potassium hydroxide in 75 ml of anhydrous methanol was added 10 g of 2-[5-(p-nitrophenoxymethyl)-1,2,4-oxadiazol-3-yl]-2',4',6'-trichloroacetanilide. The mixture was heated under reflux for 2 hours. The reaction did not stop with 3-[(p-nitro-phenoxy)acetamido]-1-(2,4,6-trichlorophenyl)-2-pyrazolin-5-one but proceeded further (Smiles rearrangement) to give 3-(p-nitroanilino)-1-(2,4,6-trichlorophenyl)-2-pyrazolin-5-one. At the end of the reaction, the mixture was allowed to cool to room temperature, acidified with 10 ml of acetic acid, diluted with 70 ml of water, and then allowed to stand at room temperature overnight. The product was collected, washed with water and ethanol, and dried. There was obtained 3.8 g (43%) of 3-(p-nitroanilino)-1-(2,4,6-trichlorophenyl)-2-pyrazolin-5-one as yellow crystals, mp 295°-298° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 hours

Sources & evidence

ORD record
ord-e8bdf36b797948ebaa1b501bcf0d836c
Source dataset
uspto-grants-1982_08
Patent number
US04345085

Reaction notes

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