Urea → Methyl 5-(2-amino-1,3-oxazol-5-yl)thiophene-3-carboxylate

HRID 1914579

Reaktionsgleichung

Reaktionsgleichung von HRID 1914579
[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([C:10](=[O:13])[CH2:11]Br)[S:7][CH:6]=1)=[O:4].[NH2:14][C:15]([NH2:17])=O>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([C:10]2[O:13][C:15]([NH2:17])=[N:14][CH:11]=2)[S:7][CH:6]=1)=[O:4]

Komponenten

4

Edukt 2

HCID 1176UreaHCID 539045465-(2-Bromo-acetyl)-thiophene-3-carboxylic acid methyl ester

Produkt 1

HCID 58110273Methyl 5-(2-amino-1,3-oxazol-5-yl)thiophene-3-carboxylateAusbeute 100,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

5-(2-Bromo-acetyl)-thiophene-3-carboxylic acid methyl ester (0.261 g, 0.99 mmol) was dissolved in DMF (4 mL) and urea (0.131 g, 2.18 mmol) was added. The vessel was purged with nitrogen then sealed and heated by microwave irradiation at 140° C. for 10 minutes. The resultant mixture was diluted with water and extracted with ethyl acetate (×3). The organic phase was washed with lithium chloride (15% aqueous solution) then dried over sodium sulfate, filtered and evaporated to give crude 5-(2-amino-oxazol-5-yl)-thiophene-3-carboxylic acid methyl ester as an orange-brown solid (0.224 g).

Aufarbeitung

  1. customThe vessel was purged with nitrogen
  2. customthen sealed
  3. additionThe resultant mixture was diluted with water
  4. extractionextracted with ethyl acetate (×3)
  5. washThe organic phase was washed with lithium chloride (15% aqueous solution)
  6. dry with materialthen dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-b9aa7d7fcde14863b9e04327bc67a686
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08614209B2

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