Hydrochloric Acid → Ethyl 5-(aminomethyl)-1,3,4-oxadiazole-2-carboxylate

HRID 966424Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 966424
C(OC([NH:8][CH2:9][C:10]1[O:14][C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:12][N:11]=1)=O)(C)(C)C.Cl.C(Cl)Cl.C(OCC)(=O)C>O1CCOCC1>[NH2:8][CH2:9][C:10]1[O:14][C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:12][N:11]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 10084542Ethyl 5-(((tert-butoxycarbonyl)amino)methyl)-1,3,4-oxadiazole-2-carboxylateHCID 21226138Dichloromethane ethylacetate

Produkt 1

HCID 11378755Ethyl 5-(aminomethyl)-1,3,4-oxadiazole-2-carboxylateAusbeute 8,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Crude, unpurified compound 8 (5 g) is added portionwise to a 0° C. commercially available solution of hydrogen chloride in 1,4-dioxan (Aldrich, 4 M, 35 ml.) Compound 8a slowly dissolves to afford a clear yellow solution. After stirring for approximately 12 hours, the reaction mixture turns cloudy. TLC on silica using methylene chloride:ethyl acetate (9:1) as the eluent shows the starting material has been consumed. The reaction mixture is filtered and a white solid is obtained. The solid is washed exhaustively with ether (50 mL) to afford 266 mg of compound 9.

Aufarbeitung

  1. dissolutionslowly dissolves
  2. customto afford a clear yellow solution
  3. customhas been consumed
  4. filtrationThe reaction mixture is filtered
  5. customa white solid is obtained
  6. washThe solid is washed exhaustively with ether (50 mL)

Quellen und Nachweise

ORD-Eintrag
ord-9345db7ae7524d01b9cf14030e24a32f
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06951946B2

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