Reaktion #337921

Reaktionsgleichung

sodium azide

1-phenyl-2-(3-(isopropylamino)-4-nitrophenyl)acetylene

hydrochloric acid

→

desired compound

Ausbeute 80.0%

4-Phenyl-5-(3-(isopropylamino)-4-nitrophenyl)-[1,2,3]triazole

Ausbeute 80.0%

Lösungsmittel

dimethoxyethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturHeat
2. 2
   Temperaturto reflux for 2 hours
3. 3
   Extraktionextract with ethyl acetate (20 mL)
4. 4
   Waschenwash with saturated aqueous sodium chloride (2×10 mL)
5. 5
   EinengenDry organic phase over sodium sulfate and concentrate under reduced pressure
6. 6
   Wascheneluting with 1:1 ethyl acetate

Vorschrift

Add sodium azide (0.13 g) to a solution of 1-phenyl-2-(3-(isopropylamino)-4-nitrophenyl)acetylene (0.56 g) in dimethoxyethane (5 mL). Heat to reflux for 2 hours. Cool to room temperature. Add 1N hydrochloric acid (10 mL), extract with ethyl acetate (20 mL), and wash with saturated aqueous sodium chloride (2×10 mL). Dry organic phase over sodium sulfate and concentrate under reduced pressure. Subject the reside to silica gel chromatography, eluting with 1:1 ethyl acetate:hexane to provide the desired compound as a yellow solid (0.51 g, 80%).

Quelle