Methyl iodide → 3-(3,5-difluorophenyl)-4-methyl-5-(methylthio)-4H-1,2,4-triazole

HRID 639834Notes

Reaction equation

HRID 639834 reaction equation
[CH3:1]I.[F:3][C:4]1[CH:5]=[C:6]([C:11]2[N:12]([CH3:17])[C:13](=[S:16])[NH:14][N:15]=2)[CH:7]=[C:8]([F:10])[CH:9]=1.[OH-].[Na+]>CC(C)=O.O>[F:10][C:8]1[CH:7]=[C:6]([C:11]2[N:12]([CH3:17])[C:13]([S:16][CH3:1])=[N:14][N:15]=2)[CH:5]=[C:4]([F:3])[CH:9]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 703281195-(3,5-Difluoro-phenyl)-4-methyl-2,4-dihydro-[1,2,4]triazole-3-thione

Product 1

HCID 578379693-(3,5-difluorophenyl)-4-methyl-5-(methylthio)-4H-1,2,4-triazoleYield 93%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

MeI (1.4 mL, 22.4 mmol) was added to a mixture of 5-(3,5-difluorophenyl)-4-methyl-2,4-dihydro-3H-1,2,4-triazole-3-thione (5 g, 22 mmol) in acetone (80 mL). NaOH (0.9 g, 22 mmol) in H2O (20 mL) was added and the reaction was stirred for 3 h at r.t. The formed precipitate was filtered off and the solution is evaporated to half volume and the formed precipitate was filtered off and combined with the first filtrate to give 4.92 g (93%) of the title compound.

Workup

  1. filtrationThe formed precipitate was filtered off
  2. customthe solution is evaporated to half volume
  3. filtrationthe formed precipitate was filtered off

Sources & evidence

ORD record
ord-cbddd573935f4be1bb304783fea103a5
Source dataset
uspto-grants-2010_04
Patent number
US07691892B2

Reaction notes

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