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

HRID 660850

Reaction equation

HRID 660850 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[C:4]([NH:6][NH:7][C:8]([NH:10][CH:11]1[CH2:13][CH2:12]1)=[O:9])=O.Cl>[OH-].[Na+]>[Cl:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[C:4]1[N:10]([CH:11]2[CH2:13][CH2:12]2)[C:8](=[O:9])[NH:7][N:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 471621452-(2-chlorobenzoyl)-N-cyclopropylhydrazinecarboxamide

Product 1

HCID 580121355-(2-chlorophenyl)-4-cyclopropyl-2,4-dihydro-3H-1,2,4-triazol-3-one

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

7.00 g (27.6 mmol) of 2-(2-chlorobenzoyl)-N-cyclopropylhydrazinecarboxamide from Example 10A are heated under reflux for about 60 hrs in 30 ml 3 N aqueous sodium hydroxide (conversion testing by LC/MS analysis). After cooling, it is acidified with 1 N hydrochloric acid and the mixture extracted three times with ethyl acetate. The combined organic phases are washed twice with saturated sodium hydrogen carbonate solution, dried over magnesium sulphate, filtered and concentrated. 3.32 g (48% of theory) of the target compound are thus obtained.

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture extracted three times with ethyl acetate
  3. washThe combined organic phases are washed twice with saturated sodium hydrogen carbonate solution
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custom3.32 g (48% of theory) of the target compound are thus obtained

Sources & evidence

ORD record
ord-1005fd404d3446ca93ee44b49713812a
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Linked notes

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