Reaktion #329441

Reaktionsgleichung

azidoacetic acid ethyl ester

2-chloroacrylonitrile

hydrochloric acid

→

(4-Cyano-1H-1,2,3-triazol-1-yl)acetic acid ethyl ester

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with ethyl acetate
2. 2
   TrocknenThe organic phase is dried over sodium sulfate
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated in vacuo
5. 5
   workup.ADDITION50 ml ethanol and 10 drops of conc. sulfuric acid are added to the residue
6. 6
   Temperaturunder reflux for 16 h
7. 7
   Einengenthe reaction mixture is concentrated in vacuo, ethyl acetate
8. 8
   workup.ADDITIONis added to the residue
9. 9
   Waschenthe suspension is washed with half-concentrated sodium bicarbonate solution
10. 10
    Trocknenthe organic phase is dried over sodium sulfate
11. 11
    SonstigeThe solvent is removed completely on a rotary evaporator
12. 12
    Sonstigethe solid is dried in vacuo

Vorschrift

4.1 g (31.9 mmol) azidoacetic acid ethyl ester and 2.8 g (31.9 mmol) 2-chloroacrylonitrile are stirred in 32 ml water at a bath temperature of 80° C. for 16 h. After cooling to RT, the solution is rendered acid with 1 N hydrochloric acid and extracted with ethyl acetate. The organic phase is dried over sodium sulfate, filtered and concentrated in vacuo. 50 ml ethanol and 10 drops of conc. sulfuric acid are added to the residue and the mixture is stirred under reflux for 16 h. For working up, the reaction mixture is concentrated in vacuo, ethyl acetate is added to the residue, the suspension is washed with half-concentrated sodium bicarbonate solution and the organic phase is dried over sodium sulfate. The solvent is removed completely on a rotary evaporator and the solid is dried in vacuo.

Quelle