Reaktionsgleichung
O=P(Cl)(Cl)Cl.[CH:6]1[C:19]2[CH:18]([C:20]([NH2:22])=O)[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[O:11][C:10]=2[CH:9]=[CH:8][CH:7]=1.[NH4+].[OH-]>>[CH:16]1[C:17]2[CH:18]([C:20]#[N:22])[C:19]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[O:11][C:12]=2[CH:13]=[CH:14][CH:15]=1Komponenten
Versuchsvorschrift
POCl3 (25 mL) was added to crystalline 9H-Xanthene-9-carboxamide [26] (1.5 g, 6.65 mmol) while stirring. The solution was then heated at reflux (45 min), when TLC showed complete absence of starting material. The solution was then poured into a mixture of crushed ice and NH4OH with vigorous stirring. The solution was stirred (15 min) and excess of NH4OH was added to keep the solution alkaline. The solid formed was extracted with ether (3×50 ml). The combined ether extracts were washed with water and brine, dried (MgSO4) and evaporated under reduced pressure to give an yellow oil which crystallized immediately. The product was purified by mplc using pet. ether: acetone (8:2) as eluent to give 1.2 g (87%) 9H-Xanthene-9-carbonitrile as colorless needles, mp 97-98° C. (EtOH).
Aufarbeitung
- temperatureThe solution was then heated
- temperatureat reflux (45 min), when TLC
- stirringThe solution was stirred (15 min)
- customThe solid formed
- extractionwas extracted with ether (3×50 ml)
- washThe combined ether extracts were washed with water and brine
- dry with materialdried (MgSO4)
- customevaporated under reduced pressure
- customto give an yellow oil which
- customcrystallized immediately
- customThe product was purified by mplc
Quellen und Nachweise
- ORD-Eintrag
- ord-a14edc5c6e3548f399a18b202faa31c7
- Quelldatensatz
- uspto-grants-2004_10
- Patentnummer
- US06806283B2
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