N-Phthaloylglycine → 2-[(3-Ethyl-1,2,4-oxadiazol-5-yl)methyl]-1H-isoindole-1,3(2H)-dione

HRID 1087861

Reaktionsgleichung

Reaktionsgleichung von HRID 1087861
C(N1C=CN=C1)(N1C=CN=C1)=O.[C:13]1(=[O:27])[N:17]([CH2:18][C:19]([OH:21])=O)[C:16](=[O:22])[C:15]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:14]12.[C:28](=[N:32]O)([NH2:31])[CH2:29][CH3:30]>C1COCC1>[CH2:29]([C:28]1[N:32]=[C:19]([CH2:18][N:17]2[C:13](=[O:27])[C:14]3=[CH:26][CH:25]=[CH:24][CH:23]=[C:15]3[C:16]2=[O:22])[O:21][N:31]=1)[CH3:30]

Komponenten

5

Edukt 3

HCID 20825N-PhthaloylglycineHCID 682631,1'-CarbonyldiimidazoleHCID 4092053N-Hydroxypropionimidamide

Produkt 1

HCID 140319642-[(3-Ethyl-1,2,4-oxadiazol-5-yl)methyl]-1H-isoindole-1,3(2H)-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

At 40° C., a suspension of 26.0 g of carbonyldiimidazole in 250 ml of THF is added to a solution of 65.7 g of phthalimidoacetic acid in 500 ml of THF (absolute). After about one hour, no release of gas can be observed any longer. At this point in time, a solution of 28.2 g of propionamidoxime in 50 ml of THF-- is added, and the mixture is stirred at room temperature for 24 hours. After the precipitate has been filtered off, the filtrate is concentrated under vacuum and, after addition of 500 ml of dry xylene, is heated under reflux for 6 hours on a water trap. The still hot solution is separated from the oily residue and concentrated under vacuum. Crystallization from EtOH yields 31.5 g (76.5%, based on carbonyldiimidazole) of oxadiazole having a melting point of 106°-107° C.

Aufarbeitung

  1. filtrationAfter the precipitate has been filtered off
  2. concentrationthe filtrate is concentrated under vacuum
  3. additionafter addition of 500 ml of dry xylene
  4. temperatureis heated
  5. temperatureunder reflux for 6 hours on a water trap
  6. customThe still hot solution is separated from the oily residue
  7. concentrationconcentrated under vacuum
  8. customCrystallization from EtOH
  9. customyields 31.5 g (76.5%, based on carbonyldiimidazole) of oxadiazole having a melting point of 106°-107° C.

Quellen und Nachweise

ORD-Eintrag
ord-f0d8e9846bb64ddcbd011b37293145ff
Quelldatensatz
uspto-grants-1990_10
Patentnummer
US04960777

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