Ethanol → Ethyl 2,1,3-benzoxadiazole-5-carboxylate

HRID 1258315Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1258315
[N:1]1[O:2][N:3]=[C:4]2[CH:9]=[C:8]([C:10]#N)[CH:7]=[CH:6][C:5]=12.[OH:12]S(O)(=O)=O.[CH3:17][CH2:18][OH:19]>>[N:1]1[O:2][N:3]=[C:4]2[CH:9]=[C:8]([C:10]([O:19][CH2:18][CH3:17])=[O:12])[CH:7]=[CH:6][C:5]=12

Komponenten

4

Edukt 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 27354522,1,3-Benzoxadiazole-5-carbonitrile

Produkt 1

HCID 2736368Ethyl 2,1,3-benzoxadiazole-5-carboxylateAusbeute 75 %

Versuchsvorschrift

To a solution of benzo[c][1,2,5]oxadiazole-5-carbonitrile (700 mg, 1.33 mol) in EtOH (100 mL) was added H2SO4 (20 mL) and the reaction mixture was refluxed for 14 h. The reaction was concentrated in vacuo and the residue was diluted with water (50 mL), and extracted with DCM (2×100 mL). The combined organic layers were dried over magnesium sulfate, filtered, and then concentrated in vacuo to afford ethyl benzo[c][1,2,5]oxadiazole-5-carboxylate (0.7 g, 75%) as a yellow, sticky solid.

Aufarbeitung

  1. temperaturethe reaction mixture was refluxed for 14 h
  2. concentrationThe reaction was concentrated in vacuo
  3. additionthe residue was diluted with water (50 mL)
  4. extractionextracted with DCM (2×100 mL)
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ee07ba6d49ea4b1ea04ecb762b4b34f2
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08466148B2

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