Hydrochloric Acid → methyl 1H-1,3-benzodiazole-5-carboxylate

HRID 1419122

Reaktionsgleichung

Reaktionsgleichung von HRID 1419122
[N:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([OH:12])=[O:11])=[CH:9][C:4]=2[NH:3][CH:2]=1.[CH3:13]O.Cl>O1CCOCC1>[N:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([O:12][CH3:13])=[O:11])=[CH:9][C:4]=2[NH:3][CH:2]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 4594565-Benzimidazolecarboxylic acid

Produkt 1

HCID 2779733methyl 1H-1,3-benzodiazole-5-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 10 g of 5-benzimidazolecarboxylic acid, 150 ml of methanol and 100 ml of a 4N solution of hydrogen chloride in 1,4-dioxane was agitated ultrasonically for 4 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, after which 300 ml of methanol and 3.5 g of lithium borohydride were added to the residue and the mixture was stirred for 1 hour. The solvent was then removed by evaporation under reduced pressure and the residue was mixed with an aqueous solution of sodium chloride, after which it was extracted with ethyl acetate. The solvent was removed by distillation under reduced pressure, to give 5.44 g of the title compound, melting at 136°-138° C.

Aufarbeitung

  1. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  2. additionafter which 300 ml of methanol and 3.5 g of lithium borohydride were added to the residue
  3. stirringthe mixture was stirred for 1 hour
  4. customThe solvent was then removed by evaporation under reduced pressure
  5. additionthe residue was mixed with an aqueous solution of sodium chloride
  6. extractionafter which it was extracted with ethyl acetate
  7. customThe solvent was removed by distillation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c11418e650954deeae25fbb9abf65142
Quelldatensatz
uspto-grants-1999_03
Patentnummer
US05886014

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