Ethyl 5-amino-1-phenyl-1H-1,2,3-triazole-4-carboxylate → HCID 178470432, compound

HRID 27687

Reaction equation

HRID 27687 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[N:4][C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].[Na]>C(O)C>[CH2:16]([O:15][C:13]([C:3]1[NH:4][N:5]=[N:1][C:2]=1[NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:14])[CH3:17]

Participants

4

Reactant 2

HCID 253349Ethyl 5-amino-1-phenyl-1H-1,2,3-triazole-4-carboxylateHCID 5360545Sodium

Product 1

HCID 178470432HCID 178470432, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 5-amino-1-phenyl-1,2,3-triazole-4-carboxylate (3.13 g; 0.0135 mole) was stirred at reflux with a solution of sodium (0.31 g; 0.135 atom) in ethanol (20 ml) for 3 hrs. and the mixture evaporated to dryness. The residual solid was dissolved in warm water, acidified and the precipitate filtered off to give 2.622 g (84%) of the title compound of mp 126-127° C. Recrystallisation from 90% ethanol gave material of mp 131-132° C. (lit mp 129-130° C.; O. Dimroth Annalen 364 183 [1909])

Workup

  1. customand the mixture evaporated to dryness
  2. dissolutionThe residual solid was dissolved in warm water
  3. filtrationthe precipitate filtered off

Sources & evidence

ORD record
ord-97c58caf5a6441a8b0a0629adfc2aa41
Source dataset
uspto-grants-1980_09
Patent number
US04223032

Linked notes

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