Potassium Carbonate → 4-(Pentafluorophenyl)urazole

HRID 1902895

Reaktionsgleichung

Reaktionsgleichung von HRID 1902895
[F:1][C:2]1[C:7]([NH:8][C:9](=[O:17])[NH:10][NH:11][C:12](OCC)=[O:13])=[C:6]([F:18])[C:5]([F:19])=[C:4]([F:20])[C:3]=1[F:21].C(=O)([O-])[O-].[K+].[K+]>O>[F:18][C:6]1[C:7]([N:8]2[C:9](=[O:17])[NH:10][NH:11][C:12]2=[O:13])=[C:2]([F:1])[C:3]([F:21])=[C:4]([F:20])[C:5]=1[F:19]

Komponenten

4

Edukt 2

HCID 11430Potassium CarbonateHCID 129043764-(Pentafluorophenyl)-1-carbethoxysemicarbazide

Produkt 1

HCID 129043794-(Pentafluorophenyl)urazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

4-(Pentafluorophenyl)-1-carbethoxysemicarbazide, 2.13 g (0.0068 M), and potassium carbonate, 0.938 g (0.0068 M), are added to 75 ml of water. The mixture is heated at 70° C. under N2 about 12 hours. The solution is cooled in an ice bath and filtered to remove a trace of starting material. The pH of the solution is adjusted to pH 7 with concentrated HCl and extracted with ethyl acetate to remove a product which is less polar than the urazole in the TLC system, chloroform/ethyl acetate/acetic acid (5/5/1). The pH of the solution is reduced to 1 or 2 with concentrated HCl and then extracted with ethyl acetate. About 1/3 of a volume of toluene is added to the ethyl acetate and the solvents evaporated. The resulting crude solid weighs 0.569 g. The product is purified by two crystallizations from ethyl acetate/toluene (1/3 by vol). The yield of purified material is 0.476 g. It is recrystallized from H2O, mp 223°-226°.

Aufarbeitung

  1. temperatureThe solution is cooled in an ice bath
  2. filtrationfiltered
  3. customto remove a trace of starting material
  4. extractionextracted with ethyl acetate
  5. customto remove a product which
  6. extractionextracted with ethyl acetate
  7. additionAbout 1/3 of a volume of toluene is added to the ethyl acetate
  8. customthe solvents evaporated
  9. customThe product is purified by two crystallizations from ethyl acetate/toluene (1/3 by vol)
  10. customIt is recrystallized from H2O, mp 223°-226°

Quellen und Nachweise

ORD-Eintrag
ord-e59b3d298b554a8d87947dbde04ac928
Quelldatensatz
uspto-grants-1982_12
Patentnummer
US04366320

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