Diethyl Ether → 2-amino-4-(thien-2-yl)-4H-oxazol-5-one hydrochloride

HRID 2352678Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2352678
S(Cl)([Cl:3])=O.[NH2:5][C:6]([NH:8][CH:9]([C:13]1[S:14][CH:15]=[CH:16][CH:17]=1)[C:10]([OH:12])=[O:11])=O.CCOCC>C(#N)C>[ClH:3].[NH2:5][C:6]1[O:11][C:10](=[O:12])[CH:9]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)[N:8]=1

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 24386Thionyl ChlorideHCID 129116992-[(Aminocarbonyl)amino]-2-(thien-2-yl)acetic acid

Produkt 1

HCID 198432152-amino-4-(thien-2-yl)-4H-oxazol-5-one hydrochlorideAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Thionyl chloride (0.87 g, 7.3 mmol) was added to a suspension of 2-[(aminocarbonyl)amino]-2-(thien-2-yl) acetic acid (0.60 g, 3 mmol) in dry acetonitrile (17 ml) at 0°-5° C. under a nitrogen atmosphere. After 5 minutes dry ether (29 ml) was added and the resulting slurry was stirred for 10 minutes. The precipitate was then filtered under nitrogen, and washed well with ether. The product was dried in vacuo to afford 2-amino-4-(thien-2-yl)-4H-oxazol-5-one hydrochloride (0.60 g, 92%) as a salmon pink powder; νmax (Nujol) 1878, 1745, 1725 cm-1.

Aufarbeitung

  1. filtrationThe precipitate was then filtered under nitrogen
  2. washwashed well with ether
  3. customThe product was dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-bee71f857fb84cec926d20501d668100
Quelldatensatz
uspto-grants-1989_10
Patentnummer
US04877783

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