Water → Ethyl 5-amino-1-phenyl-1H-1,2,3-triazole-4-carboxylate
Reaktionsgleichung
CC[O-].[Na+].[C:5]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])#[N:6].[N:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[N+:14]=[N-:15].O>CCO>[CH2:11]([O:10][C:8]([C:7]1[N:15]=[N:14][N:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:5]=1[NH2:6])=[O:9])[CH3:12]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a freshly prepared NaOEt (1.18 mmol) solution in EtOH (0.75 mL) is added ethyl cyanoacetate (100 mg, 0.88 mmol) at 0° C. After stirring at 0° C. for 10 min., azido-benzene (100 mg, 0.84 mmol, prepared according to the method reported by M. Kurumi et al. Heterocycles. 2000, 53, 2809) is added. After the addition, the mixture is allowed to slowly warm up to room temperature and stirred for 14 h. The mixture is then treated with water (3 mL) and extracted with EtOAc (3×3 mL). The combined extracts is concentrated and purified by flash column chromatography (silica gel, 0%-70% EtOAc/hexane) to provide 5-amino-1-phenyl-1H-[1,2,3]triazole-4-carboxylic acid ethyl ester as a white solid (100 mg, 51%). HPLC-MS calculated C11H12N4O2 (M+1+): 233.1. Found: 233.1.
Aufarbeitung
- addition2000, 53, 2809) is added
- additionAfter the addition
- temperatureto slowly warm up to room temperature
- stirringstirred for 14 h
- extractionextracted with EtOAc (3×3 mL)
- concentrationThe combined extracts is concentrated
- custompurified by flash column chromatography (silica gel, 0%-70% EtOAc/hexane)
Quellen und Nachweise
- ORD-Eintrag
- ord-fbc9e9fd187b45048606f58850066015
- Quelldatensatz
- uspto-grants-2012_04
- Patentnummer
- US08158634B2
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