Citric Acid → 3H-1,2,4-Triazol-3-one, 2,4-dihydro-5-(4-chlorophenyl)-4-methyl-

HRID 660853Notes

Reaction equation

HRID 660853 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([NH:8][NH:9][C:10]([NH:12][CH3:13])=[O:11])=O)=[CH:4][CH:3]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[OH-].[Na+]>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]2[N:12]([CH3:13])[C:10](=[O:11])[NH:9][N:8]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 311Citric AcidHCID 3116972-(4-chlorobenzoyl)-N-methylhydrazinecarboxamide

Product 1

HCID 30877493H-1,2,4-Triazol-3-one, 2,4-dihydro-5-(4-chlorophenyl)-4-methyl-

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

400 mg (1.78 mmol) of 2-(4-chlorobenzoyl)-N-methylhydrazinecarboxamide from Example 34A are heated under reflux overnight in 7 ml 3 N aqueous sodium hydroxide. After cooling, it is adjusted to pH ca. 11 with aqueous citric acid solution and the resulting precipitate filtered off, washed with water and dried in vacuo. 350 mg (95% of theory) of the target compound are thus obtained.

Workup

  1. temperatureAfter cooling
  2. filtrationthe resulting precipitate filtered off
  3. washwashed with water
  4. customdried in vacuo
  5. custom350 mg (95% of theory) of the target compound are thus obtained

Sources & evidence

ORD record
ord-0ad7c5616fb3423c8b1cdef884be1c64
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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