Reaktionsgleichung
[CH3:1][C:2]1[N:6]=[CH:5][NH:4][N:3]=1.Cl[C:8]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:9]=1[C:10]#[N:11].C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[CH3:1][C:2]1[N:6]=[CH:5][N:4]([C:8]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:9]=2[C:10]#[N:11])[N:3]=1Komponenten
Reaktionsbedingungen
- Temperatur
- 70 °C
Versuchsvorschrift
Step G (1): A mixture of 3-methyl-1H-1,2,4-triazole (6.83 g, 82 mmol), 2-chloro-5-nitrobenzonitrile (15 g, 82 mmol), and potassium carbonate (34.1 g, 246 mmol) in anhydrous acetonitrile (200 mL) was heated at 70° C. for 16 h. The dark brown reaction mixture was allowed to cool to rt and was poured into water (500 mL). The aqueous mixture was extracted with EtOAc (3×200 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue was purified using silica gel chromatography (40-100% ethyl acetate/hexane, linear gradient) to afford 2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrobenzonitrile (10.9 g, 58% yield). LC-MS (M+H)+=230.1. 1H NMR (500 MHz, chloroform-D) δ ppm 2.53 (s, 3 H) 8.10 (d, J=9.16 Hz, 1 H) 8.56 (dd, J=9.16, 2.44 Hz, 1 H) 8.68 (d, J=2.44 Hz, 1 H) 8.93 (s, 1 H).
Aufarbeitung
- temperatureto cool to rt
- extractionThe aqueous mixture was extracted with EtOAc (3×200 mL)
- washThe combined organic layers were washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe crude residue was purified
Quellen und Nachweise
- ORD-Eintrag
- ord-b1a653174da24ee99c2ec442053344d2
- Quelldatensatz
- uspto-grants-2013_01
- Patentnummer
- US08349880B2
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