Hydrochloric Acid → 3-(4-Chlorophenyl)-4-cyclopropyl-1H-1,2,4-triazol-5(4H)-one

HRID 660847Notes

Reaction equation

HRID 660847 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][NH:9][C:10]([NH:12][CH:13]2[CH2:15][CH2:14]2)=[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]([CH:13]3[CH2:15][CH2:14]3)[C:10](=[O:11])[NH:9][N:8]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 471338702-(4-chlorobenzoyl)-N-cyclopropylhydrazinecarboxamide

Product 1

HCID 580121993-(4-Chlorophenyl)-4-cyclopropyl-1H-1,2,4-triazol-5(4H)-one

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

14.65 g (57.7 mmol) of 2-(4-chlorobenzoyl)-N-cyclopropylhydrazinecarboxamide from Example 2A are heated under reflux overnight in 60 ml 2 N aqueous sodium hydroxide. After cooling, the mixture is acidified to pH 1 with 2 N hydrochloric acid and extracted with ethyl acetate. The organic phase is dried over sodium sulphate, filtered and concentrated. The residue is stirred with dichloromethane, and the resulting precipitate filtered off, then washed with dichloromethane and dried in vacuo. 10.9 g (69% of theory) of the target compound are thus obtained.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase is dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. filtrationthe resulting precipitate filtered off
  7. washwashed with dichloromethane
  8. customdried in vacuo
  9. custom10.9 g (69% of theory) of the target compound are thus obtained

Sources & evidence

ORD record
ord-0b52c528eda44a09a45af8825fd2d1bc
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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