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

HRID 27686

Reaction equation

HRID 27686 reaction equation
[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]

Participants

6

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 69319AzidobenzeneHCID 5360545Sodium

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

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]).

Workup

  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

Sources & evidence

ORD record
ord-b3e067cf1f534ffe8363abbafa8f7d65
Source dataset
uspto-grants-1980_09
Patent number
US04223032

Linked notes

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