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Sodium Hydroxide → 5-n-Butyl-4-(4-carboxybenzyl)-2,4-dihydro-2-[2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one

HRID 36240
Notes
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Reaction equation

HRID 36240 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]([O:30]C)=[O:29])=[CH:24][CH:23]=2)[C:7](=[O:20])[N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]([F:19])([F:18])[F:17])[N:9]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+]>C1COCC1.CO>[CH2:1]([C:5]1[N:6]([CH2:21][C:22]2[CH:23]=[CH:24][C:25]([C:28]([OH:30])=[O:29])=[CH:26][CH:27]=2)[C:7](=[O:20])[N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]([F:19])([F:17])[F:18])[N:9]=1)[CH2:2][CH2:3][CH3:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 199394365-n-Butyl-2,4-dihydro-4-[4-(methoxycarbonyl)benzyl]-2-[2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one

Product 1

HCID 199394615-n-Butyl-4-(4-carboxybenzyl)-2,4-dihydro-2-[2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-oneYield 96%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent
HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
60 °C

Procedure

A solution of 25 mg (0.0577 mmole) of 5-n-butyl-2,4-dihydro-4-[4-(methoxycarbonyl)benzyl]-2-[2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one (from Example 26) in 0.25 mL of THF was treated with 0.25 mL of 1N sodium hydroxide in methanol, and the resulting solution was stirred overnight at 60° C. Volatiles were removed by evaporation, and the residue was taken up in 1 mL of methanol and acidified to pH 1.5 by addition of 1N HCl in methanol. The mixture was concentrated to dryness. The residue was leached with chloroform. The CHCl3 solution was dried over anhydrous sodium sulfate, filtered through Celite, and concentrated in vacuo to give 23 mg (96%) of the title compound as a colorless, glassy solid; homogeneous by TLC in 9:1 CH2Cl2 --MeOH; mass spectrum (FAB) m/e 420 (M+1)+.

Workup

  1. customVolatiles were removed by evaporation
  2. additionacidified to pH 1.5 by addition of 1N HCl in methanol
  3. concentrationThe mixture was concentrated to dryness
  4. dry with materialThe CHCl3 solution was dried over anhydrous sodium sulfate
  5. filtrationfiltered through Celite
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ec6e9dc321a442e3abca84b4aab65d41
Source dataset
uspto-grants-1995_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05411980

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes