Acetonitrile → 2-(4-Nitrophenyl)-2H-tetrazole
Reaktionsgleichung
[NH:1]1[CH:5]=[N:4][N:3]=[N:2]1.C(#N)C.F[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>>[N+:16]([C:13]1[CH:14]=[CH:15][C:10]([N:2]2[N:3]=[N:4][CH:5]=[N:1]2)=[CH:11][CH:12]=1)([O-:18])=[O:17]Komponenten
Reaktionsbedingungen
- Temperatur
- 110 °C
Versuchsvorschrift
1H-tetrazole in acetonitrile solution (0.45M, 19 mL, 8.5 mmol) was combined with 4-fluoro-nitrobenzene (1 g, 7.09 mmol) in a 40 mL pressure tube, followed by addition of potassium carbonate. The tube was sealed and heated at 110° C. overnight (caution: build-up of pressure possible; use a safety shield). Pressure buildup was observed. The pressure was released carefully. The reaction was concentrated to dryness and diluted with water. The aqueous mixture was extracted 4 times with DCM. The combine organic layers were dried over sodium sulfate, filtered, concentrated and purified by column chromatography through a 40 gram biotage silica gel cartridge eluted with 5-20% ethyl acetate/hexanes (gradient) to give the product as white solid. LRMS talc: 191.0; obs: 192.3 (M+1).
Aufarbeitung
- customThe tube was sealed
- concentrationThe reaction was concentrated to dryness
- additiondiluted with water
- extractionThe aqueous mixture was extracted 4 times with DCM
- dry with materialThe combine organic layers were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- custompurified by column chromatography through a 40 gram biotage silica gel cartridge
- washeluted with 5-20% ethyl acetate/hexanes (gradient)
Quellen und Nachweise
- ORD-Eintrag
- ord-e67dae7897c9481c989f12cf4c086f31
- Quelldatensatz
- uspto-grants-2013_01
- Patentnummer
- US08343990B2
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