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

HRID 660894Notes

Reaction equation

HRID 660894 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][NH:9][C:10]([NH:12][CH2:13][CH:14]=[CH2:15])=[O:11])=O)=[CH:4][CH:3]=1.Cl>[OH-].[Na+]>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]2[N:12]([CH2:13][CH:14]=[CH2:15])[C:10](=[O:11])[NH:9][N:8]=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

26.80 g (105.6 mmol) of 2-(4-chlorobenzoyl)-N-allylhydrazinecarboxamide from Example 206A are heated overnight under reflux in 211 ml 3 N aqueous sodium hydroxide. After cooling, it is adjusted to pH 10 with 6 N hydrochloric acid, during which the product almost completely precipitates. The precipitate is suction-filtered, washed with much water and then stirred with methanol. An insoluble white precipitate remains, which is filtered off. The filtrate is concentrated in vacuo and the residue that remains is dried under high vacuum. 21.5 g (86% of theory) of the target compound are thus obtained.

Workup

  1. temperatureAfter cooling
  2. customalmost completely precipitates
  3. filtrationThe precipitate is suction-filtered
  4. washwashed with much water
  5. filtrationwhich is filtered off
  6. concentrationThe filtrate is concentrated in vacuo
  7. customthe residue that remains is dried under high vacuum
  8. custom21.5 g (86% of theory) of the target compound are thus obtained

Sources & evidence

ORD record
ord-b6b142d813d745ae99ad7755200f5488
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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