Acetic acid, azido-, ethyl ester → ethyl 2-(4-cyano-1H-1,2,3-triazol-1-yl)acetate

HRID 1274504Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1274504
[N:1]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N+:2]=[N-:3].Cl[C:11](=[CH2:14])[C:12]#[N:13]>O>[C:12]([C:11]1[N:3]=[N:2][N:1]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:14]=1)#[N:13]

Komponenten

4

Edukt 2

HCID 69480Acetic acid, azido-, ethyl esterHCID 701982-Chloroacrylonitrile

Produkt 1

HCID 54053451ethyl 2-(4-cyano-1H-1,2,3-triazol-1-yl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of ethyl 2-azidoacetate (1.29 g) and 2-chloroacrylonitrile (1.75 g) in water (10 ml) is stirred at about 80° C. for 16 hours. After cooling, the product is extracted with dichloromethane and the concentrated extract is purified by means of column chromatography on silica gel 60 (6 g; eluent: toluene/ethyl acetate=4:1). The purified product (yield 1.21 g; 67% of theory) of m.p. 47-48° C. (recrystallization from toluene/hexane) is obtained after concentrating the eluate and drying.

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionthe product is extracted with dichloromethane
  3. extractionthe concentrated extract
  4. customis purified by means of column chromatography on silica gel 60 (6 g; eluent: toluene/ethyl acetate=4:1)
  5. customThe purified product (yield 1.21 g; 67% of theory) of m.p. 47-48° C. (recrystallization from toluene/hexane)
  6. customis obtained
  7. concentrationafter concentrating the eluate and
  8. customdrying

Quellen und Nachweise

ORD-Eintrag
ord-7274074ca09d4afe91718cc1127c8d38
Quelldatensatz
uspto-grants-2000_12
Patentnummer
US06156907

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