Ethanol → HCID 178467475, compound

HRID 617010Notes

Reaction equation

HRID 617010 reaction equation
[Na].C(O[C:5]([NH:7][N:8]([CH2:11][CH3:12])[C:9]#[N:10])=[O:6])C.[CH2:13]([OH:15])[CH3:14]>>[CH2:11]([N:8]1[C:9]([O:15][CH2:13][CH3:14])=[N:10][C:5]([OH:6])=[N:7]1)[CH3:12]

Participants

4

Reactant 3

HCID 702EthanolHCID 5360545SodiumHCID 53744342HCID 53744342, compound

Product 1

HCID 178467475HCID 178467475, compoundYield 60%

Procedure

To a solution of 4.6 g of sodium in 150 ml of absolute ethanol there is added dropwise at 60° C 31.4 g of 2-ethyl-2-cyanohydrazinecarboxylic acid ethyl ester. The solution is subsequently refluxed for 4 hours. From the cooled solution there precipitates, after the addition of 12 g of glacial acetic acid, sodium acetate, which is separated by filtration. The filtrate is concentrated in vacuo to dryness, and the residue is extracted with 200 ml of chloroform. The extract is again concentrated to dryness and the residue is recrystallised from cyclohexane. There is obtained 18.8 g (60% of theory) of 1-ethyl-5-ethoxy-3-hydroxy-1,2,4-triazole, m.p. 64° to 67° C.

Workup

  1. temperatureThe solution is subsequently refluxed for 4 hours
  2. customFrom the cooled solution there precipitates
  3. additionafter the addition of 12 g of glacial acetic acid, sodium acetate, which
  4. customis separated by filtration
  5. concentrationThe filtrate is concentrated in vacuo to dryness
  6. extractionthe residue is extracted with 200 ml of chloroform
  7. concentrationThe extract is again concentrated to dryness
  8. customthe residue is recrystallised from cyclohexane

Sources & evidence

ORD record
ord-592ef3dc9ecb4aa3924c399b393ec3b4
Source dataset
uspto-grants-1978_02
Patent number
US04076938

Reaction notes

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