Ethyl orthoformate → HCID 178518009, compound

HRID 1388785Notes

Reaction equation

HRID 1388785 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][NH:8][C:9]([NH2:11])=[O:10].[CH2:12](OC(OCC)OCC)C>C(O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH:12]=[N:11][C:9]([OH:10])=[N:8]1

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 1336606580714-38-1

Product 1

HCID 178518009HCID 178518009, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
15 °C

Procedure

A mixture of 31.9 g (0.21 m) of 2-pyridinylhydrazinecarboxamide and 17.50 ml of triethylorthoformate was refluxed for 6 hours with the ethanol formed as a by-product being continuously removed by distillation thereby maintaning the reaction temperature at 130°-140° C. At the completion of the reaction, the reaction mixture was cooled to 15° C. and the solid 1-(2-pyridinyl)-1H-1,2,4-triazol-3-ol product was recovered by filtration. The product after washing with methylene chloride was recovered in a yield of 25.2 g (74 percent of theoretical). The product melted at 260°-262° C. and upon analysis was found to have carbon, hydrogen and nitrogen contents of 52.26, 3.90 and 34.79 percent, respectively, as compared with the theoretical contents of 51.89, 3.73 and 34.55 percent, respectively, calculated for the above named compound.

Workup

  1. customformed as a by-product being
  2. customcontinuously removed by distillation
  3. customat 130°-140° C
  4. customAt the completion of the reaction
  5. filtrationthe solid 1-(2-pyridinyl)-1H-1,2,4-triazol-3-ol product was recovered by filtration
  6. washThe product after washing with methylene chloride
  7. customwas recovered in a yield of 25.2 g (74 percent of theoretical)

Sources & evidence

ORD record
ord-1ae51b89e3144fa5811487fd99420fd8
Source dataset
uspto-grants-1984_02
Patent number
US04433148

Reaction notes

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