Reaktionsgleichung
F[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[C:10](=[O:13])([O-])[O-:11].[K+].[K+].C1O[CH2:32][CH2:31]OCCOCCOCCOCCOC1.[CH3:34][N:35]([CH3:38])C=O>C(OCC)(=O)C>[C:4]([C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[N:35]1[C:38]2[C:6](=[C:3]([CH3:4])[CH:2]=[CH:9][CH:8]=2)[CH:7]=[C:34]1[C:10]([O:11][CH2:31][CH3:32])=[O:13])#[N:5]Komponenten
Reaktionsbedingungen
- Temperatur
- 150 °C
Versuchsvorschrift
A mixture of the title 2 compound (2.710 g, 13.334 mmol, 1 eq), 2-fluorobenzonitrile (6.460 g, 50.336 mmol, 4 eq), potassium carbonate (3.686 g, 26.668 mmol, 2 eq), 18-Crown-6 (881 mg, 3.334 mmol, 0.25 eq) and dimethylformamide (13.33 mL, 1M) was stirred at 150° C. for a total of 31 hours. At 14 hours, more 2-fluorobenzonitrile (2.232 g, 18.429 mmol, 1.38 eq) was added and at 17 hours, additional 18-Crown-6 (400 mg, 0.113 eq) was added. The mixture was cooled and diluted with ethyl acetate. After filtration, the filtrate was washed with pH=4 buffer and saturated sodium chloride, dried (magnesium sulfate) and concentrated. The remaining material was chromatographed on silica gel eluting with Hexane:ether (8:1) to give the title compound (2.026 g, 50%).
Aufarbeitung
- waitAt 14 hours
- temperatureThe mixture was cooled
- filtrationAfter filtration
- washthe filtrate was washed with pH=4 buffer
- dry with materialsaturated sodium chloride, dried (magnesium sulfate)
- concentrationconcentrated
- customThe remaining material was chromatographed on silica gel eluting with Hexane:ether (8:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-68eda19ed41d440e9d72332368f047ea
- Quelldatensatz
- uspto-grants-1997_04
- Patentnummer
- US05616591
Verknüpfte Notizen
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