Ethyl cyanoacetate → Ethyl 5-amino-1-phenyl-1H-1,2,3-triazole-4-carboxylate

HRID 27686

Reaktionsgleichung

Reaktionsgleichung von HRID 27686
[Na].[C:2]1([N:8]=[N+:9]=[N-:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:11]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])#[N:12]>C(O)C.O>[NH2:12][C:11]1[N:8]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:9]=[N:10][C:13]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Komponenten

6

Edukt 3

HCID 7764Ethyl cyanoacetateHCID 69319AzidobenzeneHCID 5360545Sodium

Produkt 1

HCID 253349Ethyl 5-amino-1-phenyl-1H-1,2,3-triazole-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

A solution of sodium (2.04 g; 0.089 mole) in ethanol (50 ml) was added to a mixture of phenyl azide (11.9 g; 0.1 mole) and ethyl cyanoacetate (11.3 g; 0.1 mole) and the product gently warmed to 45° C. with stirring for 5 mins. After stirring at ambient temperature for a further 15 minutes the flask was immersed in water at room temperature for 3 hrs. A white solid separated which was filtered off after dilution of the mixture with water and washed with water. Recrystallisation from ethanol gave 18.4 g. (79%) of material of mp 124.5-125.5° C. (lit mp 126°; B. R. Brown, D. L. Hammick and S. G. Heritage J. Chem. Soc. 3820 [1953]).

Aufarbeitung

  1. stirringAfter stirring at ambient temperature for a further 15 minutes the flask
  2. customA white solid separated which
  3. filtrationwas filtered off after dilution of the mixture with water
  4. washwashed with water
  5. customRecrystallisation from ethanol
  6. customgave 18.4 g

Quellen und Nachweise

ORD-Eintrag
ord-b3e067cf1f534ffe8363abbafa8f7d65
Quelldatensatz
uspto-grants-1980_09
Patentnummer
US04223032

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