Potassium Hydroxide → HCID 178516434, Verbindung

HRID 67167Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 67167
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 178516434HCID 178516434, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-e8bdf36b797948ebaa1b501bcf0d836c
Quelldatensatz
uspto-grants-1982_08
Patentnummer
US04345085

Notizen zur Reaktion

Wird geladen…