Triethylamine → 2-(4,5-Dichloro-imidazol-2-yl)-5-phenoxy-1,3,4-oxadiazole

HRID 1164376Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1164376
[C:1]1([O:7][C:8](=[O:11])[NH:9][NH2:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:12][C:13]1[N:14]=[C:15]([C:19](Cl)(Cl)Cl)[NH:16][C:17]=1[Cl:18].C(N(CC)CC)C>O1CCOCC1>[Cl:12][C:13]1[N:14]=[C:15]([C:19]2[O:11][C:8]([O:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[N:9][N:10]=2)[NH:16][C:17]=1[Cl:18]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 134791Hydrazinecarboxylic acid, phenyl esterHCID 124825734,5-Dichloro-2-(trichloromethyl)-1H-imidazole

Produkt 1

HCID 1357554452-(4,5-Dichloro-imidazol-2-yl)-5-phenoxy-1,3,4-oxadiazoleAusbeute 72,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

16.7 g (0.11 mol) of carbazic acid phenyl ester were added in portions, at room temperature, to a solution of 25.4 g (0.1 mol) of 4,5-dichloro-2-trichloromethyl-imidazole in 200 ml of dioxane. After the slightly exothermic reaction had subsided, the mixture was gradually warmed to the boil and boiled for a further 2 hours under reflux. It was then cooled to room temperature and 20.2 g (0.2 mol) of triethylamine were added dropwise. The mixture was stirred for a further 2 hours at 50° C., the insoluble constituents were filtered off and the filtrate was evaporated in vacuo. The residue was treated with water and the product was filtered off, washed with water and dried. 21.5 g (72.5% of theory) of 2-(4,5-dichloro-imidazol-2-yl)-5-phenoxy-1,3,4-oxadiazole were obtained. Melting point: 109° C. (from toluene).

Aufarbeitung

  1. customAfter the slightly exothermic reaction
  2. temperaturethe mixture was gradually warmed to the boil
  3. temperatureunder reflux
  4. filtrationthe insoluble constituents were filtered off
  5. customthe filtrate was evaporated in vacuo
  6. additionThe residue was treated with water
  7. filtrationthe product was filtered off
  8. washwashed with water
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-d7276870b2c145e1877af41999adc4fd
Quelldatensatz
uspto-grants-1983_01
Patentnummer
US04369186

Notizen zur Reaktion

Wird geladen…