Methyl iodide → 1H-1,2,4-Triazole, 4-methyl-3-(methylthio)-5-phenyl-

HRID 1885281Notes

Reaction equation

HRID 1885281 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:5][NH:4][C:3]1=[S:13].[OH-].[Na+].[CH3:16]I>C(O)C>[CH3:1][N:2]1[C:3]([S:13][CH3:16])=[N:4][N:5]=[C:6]1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 7197994-methyl-5-phenyl-4H-1,2,4-triazole-3-thiol

Product 1

HCID 2132261H-1,2,4-Triazole, 4-methyl-3-(methylthio)-5-phenyl-

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 4-methyl-5-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thione (5.0 g, 2.6×10-2 mole) and 1 molar aqueous NaOH (59 ml, 5.9×10-2 mole) was added a solution of methyl iodide (2.6 ml, 4.2×10-2 mole) and ethanol (13 ml). The reaction was stirred for 3 hours and it was then placed in the refrigerator. After standing in the refrigerator overnight, the precipitate was collected by filtration. Crystallization from isopropanol afforded colorless needles, Mp 134°-135° C.

Workup

  1. customAfter standing in the refrigerator overnight
  2. filtrationthe precipitate was collected by filtration
  3. customCrystallization from isopropanol afforded colorless needles, Mp 134°-135° C.

Sources & evidence

ORD record
ord-8affca5b04db4712b7ace3fcb407d656
Source dataset
uspto-grants-1992_09
Patent number
US05143933

Reaction notes

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