Water → Methyl 5-(3-methyl-1,2,4-oxadiazol-5-yl)-3-pyridinecarboxylate

HRID 399799

Reaktionsgleichung

Reaktionsgleichung von HRID 399799
S(Cl)(Cl)=O.[CH3:5][C:6]1[N:10]=[C:9]([C:11]2[CH:12]=[C:13]([C:17]([OH:19])=[O:18])[CH:14]=[N:15][CH:16]=2)[O:8][N:7]=1.[C:20](OCC)(=O)C.O>CO>[CH3:5][C:6]1[N:10]=[C:9]([C:11]2[CH:12]=[C:13]([C:17]([O:19][CH3:20])=[O:18])[CH:14]=[N:15][CH:16]=2)[O:8][N:7]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 24386Thionyl ChlorideHCID 189454415-(3-Methyl-1,2,4-oxadiazol-5-yl)-3-pyridinecarboxylic acid

Produkt 1

HCID 18945172Methyl 5-(3-methyl-1,2,4-oxadiazol-5-yl)-3-pyridinecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Thionyl chloride (2.5 ml) was added dropwise in methanol (25 ml) under cooling at 7°-9° C. After the mixture was stirred for 30 minutes at the same temperature, 5-(3-methyl-1,2,4-oxadiazol-5-yl)-3-pyridinecarboxylic acid (2.5 g) was added thereto and the mixture was refluxed for 3 hours. After being cooled to room temperature, the mixture was poured into a mixture of ethyl acetate (100 ml) and water (100 ml). The organic layer was successively washed with 10% potassium carbonate aqueous solution and brine, and then dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was recrystallized from diethyl ether to afford methyl 5-(3-methyl-1,2,4-oxadiazol-5-yl)-3-pyridinecarboxylate (2.12 g).

Aufarbeitung

  1. temperatureunder cooling at 7°-9° C
  2. additionwas added
  3. temperaturethe mixture was refluxed for 3 hours
  4. washThe organic layer was successively washed with 10% potassium carbonate aqueous solution and brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated in vacuo
  7. customthe residue was recrystallized from diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-c530c3da336340a2a690ddab9eb9c047
Quelldatensatz
uspto-grants-1998_10
Patentnummer
US05824691

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