Water → 1-[4-(2-Azidoethyl)phenyl]-3,5-dimethyl-4-phenyl-1H-pyrazole
Reaktionsgleichung
Cl[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]([CH3:15])=[C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:12]([CH3:22])=[N:11]2)=[CH:6][CH:5]=1.[N-:23]=[N+:24]=[N-:25].[Na+].O>CN(C)C=O>[N:23]([CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]([CH3:15])=[C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:12]([CH3:22])=[N:11]2)=[CH:6][CH:5]=1)=[N+:24]=[N-:25]Komponenten
5
Reaktionsbedingungen
- Temperatur
- 100 °C
Versuchsvorschrift
To a stirred solution of 1-[4-(2-chloroethyl)phenyl]-3,5-dimethyl-4-phenyl-1H-pyrazole (step 1, 0.34 mmol) and KI (56 mg, 0.34 mmol) in N,N-dimethylformamide (2.7 mL) was added sodium azide (44 mg, 0.68 mmol), and then the resulting mixture was stirred for 6 h at 100° C. The reaction mixture was poured into water (100 mL), and extracted with ethyl acetate/toluene (4:1). The organic layer was washed with water (50 mL) and brine (50 mL), then dried (Na2SO4). After removal of the solvent, the crude product was purified by TLC with hexane/ethyl acetate (1:1) to afford 87 mg (81%) of the title compound as yellow oil: 1H-NMR (CDCl3) δ 7.46-7.29 (9H, m), 3.55 (2H, t, J=7.3 Hz), 2.96 (2H, t, J=7.1 Hz), 2.34 (3H, s), 2.30 (3H, s).
Aufarbeitung
- extractionextracted with ethyl acetate/toluene (4:1)
- washThe organic layer was washed with water (50 mL) and brine (50 mL)
- dry with materialdried (Na2SO4)
- customAfter removal of the solvent
- customthe crude product was purified by TLC with hexane/ethyl acetate (1:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-90fc3c277fba4d1b900563fedb3cf2bf
- Quelldatensatz
- uspto-grants-2006_02
- Patentnummer
- US07001917B2
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