Diethyl Ether → Methyl 3-amino-4-methylthiophene-2-carboxylate

HRID 231644

Reaktionsgleichung

Reaktionsgleichung von HRID 231644
[CH3:1][O:2][C:3]([CH:5]1[C:9](=O)[CH:8]([CH3:11])[CH2:7][S:6]1)=[O:4].Cl.[NH2:13]O.CCOCC>C(#N)C>[NH2:13][C:9]1[C:8]([CH3:11])=[CH:7][S:6][C:5]=1[C:3]([O:2][CH3:1])=[O:4]

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 443297Hydroxyamine hydrochlorideHCID 10487456Methyl tetrahydro-4-methyl-3-oxo-2-thiophenecarboxylate

Produkt 1

HCID 123584Methyl 3-amino-4-methylthiophene-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

2-Methoxycarbonyl-4-methyl-3-oxotetrahydrothiophene (l.74 g) was dissolved in acetonitrile (13 ml) and the resulting solution was brought to the boil. To this was added hydroxylamine hydrochloride (0.69 g) and the mixture was refluxed for 5 hours. The reaction mixture was cooled in ice and dry ether (50 ml) added whereby a sticky precipitate was produced which was filtered off with the aid of kieselguhr. The kieselguhr was slurried with water and filtered, and the filtrate was basified with ammonia and extracted with ether (2 ×). The combined extracts were dried over sodium sulphate, filtered and evaporated to give the title compound, 1.lg (64%) mp 82°-83°.

Aufarbeitung

  1. temperaturethe mixture was refluxed for 5 hours
  2. temperatureThe reaction mixture was cooled in ice
  3. customwas produced which
  4. filtrationwas filtered off with the aid of kieselguhr
  5. filtrationfiltered
  6. extractionextracted with ether (2 ×)
  7. dry with materialThe combined extracts were dried over sodium sulphate
  8. filtrationfiltered
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-f762d8d93bd8435790262ce47ec8b218
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04847386

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