Hydrochloric Acid → 5-(4-chlorophenyl)-4-allyl-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 714612Notes

Reaction equation

HRID 714612 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH:10][NH:11][C:12]([NH:14][CH2:15][CH:16]=[CH2:17])=[O:13])=O)=[CH:4][CH:3]=1.Cl>[OH-].[Na+]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:14]([CH2:15][CH:16]=[CH2:17])[C:12](=[O:13])[NH:11][N:10]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 497656012-(4-chlorobenzoyl)-N-allylhydrazinecarboxamide

Product 1

HCID 497656025-(4-chlorophenyl)-4-allyl-2,4-dihydro-3H-1,2,4-triazol-3-one

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

26.8 g (106 mmol) of 2-[(4-chlorophenyl)carbonyl]-N-(prop-2-en-1-yl)hydrazinecarboxamide from Example 11A were suspended in 210 ml of 3 M aqueous sodium hydroxide solution, and the mixture was heated under reflux for 20 h. After cooling, the pH was adjusted to 10 using semiconcentrated hydrochloric acid. The precipitated colorless solid was filtered off with suction, washed with water until neutral and then stirred with methanol. By filtration, the mixture was freed from insoluble components, the filtrate was concentrated under reduced pressure on a rotary evaporator and the residue was dried under high vacuum. This gave 21.5 g (86.4% of theory) of the title compound as a colorless solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 20 h
  3. temperatureAfter cooling
  4. filtrationThe precipitated colorless solid was filtered off with suction
  5. washwashed with water until neutral and
  6. filtrationBy filtration
  7. concentrationthe filtrate was concentrated under reduced pressure on a rotary evaporator
  8. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-88b8f4e74ef5407da454b187c7cef321
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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