2-[(3-chloro-4-methyl-2-thienyl)carbonyl]-N-isobutylhydrazinecarboxamide → 5-(3-chloro-4-methyl-2-thienyl)-4-isobutyl-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 660913Notes

Reaction equation

HRID 660913 reaction equation
[Cl:1][C:2]1[C:6]([CH3:7])=[CH:5][S:4][C:3]=1[C:8]([NH:10][NH:11][C:12]([NH:14][CH2:15][CH:16]([CH3:18])[CH3:17])=[O:13])=O>[OH-].[Na+]>[Cl:1][C:2]1[C:6]([CH3:7])=[CH:5][S:4][C:3]=1[C:8]1[N:14]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:12](=[O:13])[NH:11][N:10]=1

Participants

3

Reactant 1

HCID 580122082-[(3-chloro-4-methyl-2-thienyl)carbonyl]-N-isobutylhydrazinecarboxamide

Product 1

HCID 580116455-(3-chloro-4-methyl-2-thienyl)-4-isobutyl-2,4-dihydro-3H-1,2,4-triazol-3-one

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A suspension of 1.28 g (4.42 mmol) of 2-[(3-chloro-4-methyl-2-thienyl)carbonyl]-N-isobutyl-hydrazinecarboxamide from Example 246A in 12 ml 3 N aqueous sodium hydroxide is first heated overnight under reflux. After cooling, it is filtered. The filtrate contains impure product, while the solid filtered off mainly corresponds to the educt. This solid is taken up again in ca. 15 ml of 3 N ethanolic aqueous sodium hydroxide and again heated overnight under reflux. After neutralization with 1 N hydrochloric acid and concentration, the residue together with the concentrated filtrate from the aqueous reaction is purified by preparative HPLC [Method 12]. After evaporation and drying of the product fractions, 562 mg (47% of theory) of the target compound are thus obtained.

Workup

  1. temperatureis first heated overnight
  2. temperatureunder reflux
  3. temperatureAfter cooling
  4. filtrationit is filtered
  5. filtrationwhile the solid filtered off mainly corresponds to the educt
  6. temperatureunder reflux
  7. concentrationAfter neutralization with 1 N hydrochloric acid and concentration
  8. customthe residue together with the concentrated filtrate from the aqueous reaction
  9. customis purified by preparative HPLC [Method 12]
  10. customAfter evaporation
  11. customdrying of the product fractions, 562 mg (47% of theory) of the target compound
  12. customare thus obtained

Sources & evidence

ORD record
ord-335db2d20bb94c21bb240c092343730f
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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