Methyl acetoacetate → 5-(2-Oxopropyl)-3-(3-nitrophenyl)-1,2,4-oxadiazole

HRID 916241Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 916241
[N+:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7](=[N:9][OH:10])[NH2:8])([O-:3])=[O:2].[C:14](OC)(=O)[CH2:15][C:16]([CH3:18])=[O:17]>C1(C)C=CC=CC=1>[O:17]=[C:16]([CH3:18])[CH2:15][C:14]1[O:10][N:9]=[C:7]([C:6]2[CH:11]=[CH:12][CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[N:8]=1

Komponenten

4

Edukt 2

HCID 7757Methyl acetoacetateHCID 3781554N'-hydroxy-3-nitrobenzenecarboximidamide

Produkt 1

HCID 129275385-(2-Oxopropyl)-3-(3-nitrophenyl)-1,2,4-oxadiazoleAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

In a 250 ml flask, place 10 g (0.055 m) of 3-nitrobenzamidoxime (9a), 9.6 g (0.083 m) of methyl acetoacetate (10b; R1=methyl), and 100 ml of toluene. Heat and stir the reaction mixture under reflux with a Dean-Stark trap for 16 hrs. Distill off toluene under a reduced pressure at 50-60° C. to thick oil. Add 60 ml of heptane to the oil with stirring, cool and stir at 0-5° C. for 30 min. Collect solid, wash with heptane, and dry in air to give 11.4 g (84%) of 5-(2-oxopropyl)-3-(3-nitrophenyl)-1,2,4-oxadiazole [Formula II: R1=methyl and R2=3-nitrophenyl].

Aufarbeitung

  1. temperatureHeat
  2. temperatureunder reflux with a Dean-Stark trap for 16 hrs
  3. distillationDistill off toluene under a reduced pressure at 50-60° C. to thick oil
  4. additionAdd 60 ml of heptane to the oil
  5. stirringwith stirring
  6. temperaturecool
  7. stirringstir at 0-5° C. for 30 min
  8. customCollect solid
  9. washwash with heptane
  10. customdry in air

Quellen und Nachweise

ORD-Eintrag
ord-64ddbaf77e0c4e8ea0b598069be0795a
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07268235B2

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