Acetonitrile → 2-(4-Iodophenyl)-5-(1-methyl-1H-pyrrol-2-yl)-1,3,4-oxadiazole

HRID 31425

Reaktionsgleichung

Reaktionsgleichung von HRID 31425
P(Cl)(Cl)(Cl)=O.C[N:7]([C:18]([C:20]1[NH:21][CH:22]=[CH:23][CH:24]=1)=[O:19])[NH:8][C:9](=O)[C:10]1[CH:15]=[CH:14][C:13]([I:16])=[CH:12][CH:11]=1.[C:25](#N)C>>[I:16][C:13]1[CH:14]=[CH:15][C:10]([C:9]2[O:19][C:18]([C:20]3[N:21]([CH3:25])[CH:22]=[CH:23][CH:24]=3)=[N:7][N:8]=2)=[CH:11][CH:12]=1

Komponenten

4

Edukt 3

HCID 6342AcetonitrileHCID 24813Phosphorus oxychlorideHCID 693564031h-Pyrrole-2-carboxylic acid, 1-methyl-2-(4-iodobenzoyl)hydrazide2×

Produkt 1

HCID 693159432-(4-Iodophenyl)-5-(1-methyl-1H-pyrrol-2-yl)-1,3,4-oxadiazole

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Phosphorousoxychloride (2 ml) was added to 1H-pyrrole-2-carboxylic acid, 1-methyl-2-(4-iodobenzoyl)hydrazide (Intermediate 39) (150 mg) in acetonitrile (1 ml) and the reaction heated at 100° C. for 18 hours. The cooled reaction was poured onto ice/water (60 ml) and extracted with ethyl acetate (3×40 ml). The combined extracts were reduced to dryness under vacuum and the residue applied to a bond-elut (silica) and eluted with an ethyl acetate/cyclohexane gradient to give, after evaporation of the solvent, 2-(4-iodophenyl)-5-(1-methyl-1H-pyrrol-2-yl)-1,3,4-oxadiazole.

Aufarbeitung

  1. customThe cooled reaction
  2. additionwas poured onto ice/water (60 ml)
  3. extractionextracted with ethyl acetate (3×40 ml)
  4. washeluted with an ethyl acetate/cyclohexane gradient
  5. customto give
  6. customafter evaporation of the solvent, 2-(4-iodophenyl)-5-(1-methyl-1H-pyrrol-2-yl)-1,3,4-oxadiazole

Quellen und Nachweise

ORD-Eintrag
ord-9d4bd5e7bbe54a778fb98521da9c223b
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425555B2

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