Triethyl orthoacetate → 2-(3-Iodo-4-methylphenyl)-5-methyl-1,3,4-oxadiazole

HRID 1619145

Reaktionsgleichung

Reaktionsgleichung von HRID 1619145
[I:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:5]([NH:7][NH2:8])=[O:6].[C:13](OCC)(OCC)(OCC)[CH3:14]>C(O)(=O)C>[I:1][C:2]1[CH:3]=[C:4]([C:5]2[O:6][C:13]([CH3:14])=[N:8][N:7]=2)[CH:9]=[CH:10][C:11]=1[CH3:12]

Komponenten

4

Edukt 2

HCID 66221Triethyl orthoacetateHCID 597325003-Iodo-4-methylbenzohydrazide

Produkt 1

HCID 581704972-(3-Iodo-4-methylphenyl)-5-methyl-1,3,4-oxadiazoleAusbeute 78,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A stirred mixture of 3-iodo-4-methylbenzohydrazide (preparation 55b, 5.00 g, 18.1 mmol) and triethyl orthoacetate (11.00 mL, 58.2 mmol) in acetic acid (30 mL) were heated to 150° C. in a sealed tube. After 3 hours, the mixture was cooled and concentrated in vacuo. Aqueous sodium hydrogen carbonate solution was added and the mixture was extracted with dichloromethane. The organic solution was dried (MgSO4) and the solvent was removed in vacuo. The crude material was purified by flash chromatography (2:1 hexanes/ethyl acetate) to give the title compound (4.26 g, 78%) as a white solid.

Aufarbeitung

  1. temperaturethe mixture was cooled
  2. concentrationconcentrated in vacuo
  3. additionAqueous sodium hydrogen carbonate solution was added
  4. extractionthe mixture was extracted with dichloromethane
  5. dry with materialThe organic solution was dried (MgSO4)
  6. customthe solvent was removed in vacuo
  7. customThe crude material was purified by flash chromatography (2:1 hexanes/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-a59ed7b6760e45f59b06d99d623f4516
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772288B2

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