Water → 3-biphenyl-4-yl-4-(2-fluorophenyl)-5-methylsulfanyl-4H-1,2,4-triazole

HRID 6934Notes

Reaction equation

HRID 6934 reaction equation
[C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][C:4]([C:7]2[N:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[F:19])[C:9]([SH:12])=[N:10][N:11]=2)=[CH:3][CH:2]=1.CI.[C:28](=O)([O-])[O-].[K+].[K+].O>C(#N)C>[C:1]1([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:6]=[CH:5][C:4]([C:7]2[N:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[F:19])[C:9]([S:12][CH3:28])=[N:10][N:11]=2)=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178419067HCID 178419067, compound

Product 1

HCID 220192353-biphenyl-4-yl-4-(2-fluorophenyl)-5-methylsulfanyl-4H-1,2,4-triazoleYield 72.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-Biphenyl-4-yl-4-(2-fluorophenyl)-4H-1,2,4-triazole-3-thiol (2.7 g) was dissolved in acetonitrile (50 ml), followed by addition of methyl iodide (0.967 ml) and potassium carbonate (1.07 g), and stirred at ambient temperature for 3 hours. Water was added to the reaction solution, followed by extraction with chloroform. The organic layer was washed with saturated aqueous saline and dried over anhydrous magnesium sulfate. After the solvent was evaporated under reduced pressure, the resulting solid was recrystallized from a mixture solvent of acetonitrile and ethyl acetate, to afford the entitled compound 3-biphenyl-4-yl-4-(2-fluorophenyl)-5-methylsulfanyl-4H-1,2,4-triazole as pale yellow crystal (2.03 g, 72%). The physico-chemical values are as follows.

Workup

  1. extractionfollowed by extraction with chloroform
  2. washThe organic layer was washed with saturated aqueous saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter the solvent was evaporated under reduced pressure
  5. customthe resulting solid was recrystallized from a mixture solvent of acetonitrile and ethyl acetate

Sources & evidence

ORD record
ord-ba454e8e73744cc58e8043ddd323cb9f
Source dataset
uspto-grants-2006_08
Patent number
US07084164B2

Reaction notes

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