1-Chloro-1-penten-3-one → 7-Ethyl-1,2,4-triazolo[1,5-a]pyrimidine

HRID 1290801Notes

Reaction equation

HRID 1290801 reaction equation
[NH2:1][C:2]1[N:6]=[CH:5][NH:4][N:3]=1.Cl[CH:8]=[CH:9][C:10](=O)[CH2:11][CH3:12]>C(O)(=O)C>[CH2:11]([C:10]1[N:3]2[N:4]=[CH:5][N:6]=[C:2]2[N:1]=[CH:8][CH:9]=1)[CH3:12]

Participants

4

Reactant 2

HCID 30420161-Chloro-1-penten-3-oneHCID 178418311HCID 178418311, compound

Product 1

HCID 189193537-Ethyl-1,2,4-triazolo[1,5-a]pyrimidine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3-amino-1,2,4-triazole (11.74 g) and 1-chloro-1-penten-3-one (16.5 g) in acetic acid (225 ml) was heated under reflux for 45 minutes. The reaction mixture was cooled, poured onto ice and extracted with dichloromethane. The organic layer was dried and the solvent was evaporated under reduced pressure to give 7-ethyl-1,2,4-triazolo[1,5-a]pyrimidine. Yield 11.72 g.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 45 minutes
  3. temperatureThe reaction mixture was cooled
  4. additionpoured onto ice
  5. extractionextracted with dichloromethane
  6. customThe organic layer was dried
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-0aa344644dc74068b60e34c3e9ed934b
Source dataset
uspto-grants-1998_05
Patent number
US05753665

Reaction notes

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