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

HRID 536536Notes

Reaction equation

HRID 536536 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

An amount of 26.8 g (106 mmol) of 2-[(4-chlorophenyl)carbonyl]-N-(prop-2-en-1-yl)hydrazinecarboxamide from Example 1A was suspended in 210 ml of 3M sodium hydroxide solution and heated under reflux for 20 hours. After cooling, a pH of 10 was set using half-concentrated hydrochloric acid. The colourless solid precipitated was isolated by suction filtration, washed to neutrality with water and then stirred up in methanol. The mixture was freed from insoluble constituents by filtration, the filtrate was concentrated under reduced pressure on a rotary evaporator and the residue was dried in a high vacuum. This gave 21.5 g (86.4% of theory) of the desired compound as a solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 20 hours
  3. temperatureAfter cooling
  4. customThe colourless solid precipitated
  5. customwas isolated by suction filtration
  6. washwashed
  7. filtrationThe mixture was freed from insoluble constituents by filtration
  8. concentrationthe filtrate was concentrated under reduced pressure on a rotary evaporator
  9. customthe residue was dried in a high vacuum

Sources & evidence

ORD record
ord-0efc7f8974024d3c96cd847c08df0441
Source dataset
uspto-grants-2014_10
Patent number
US08859601B2

Reaction notes

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