Methyl iodide → 3-(4-Methyl-5-(methylthio)-4H-1,2,4-triazol-3-yl)pyridine

HRID 639831Notes

Reaction equation

HRID 639831 reaction equation
CI.[CH3:3][N:4]1[C:8]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)=[N:7][NH:6][C:5]1=[S:15].[OH-].[Na+].[CH2:18](Cl)Cl>CCO>[CH3:3][N:4]1[C:5]([S:15][CH3:18])=[N:6][N:7]=[C:8]1[C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 7575824-methyl-5-(pyridin-3-yl)-4H-1,2,4-triazole-3-thiol

Product 1

HCID 404246263-(4-Methyl-5-(methylthio)-4H-1,2,4-triazol-3-yl)pyridineYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

MeI (2 mL, 32 mmol) in EtOH (10 mL) was added to a mixture of 4-methyl-5-pyridin-3-yl-2,4-dihydro-3H-1,2,4-triazole-3-thione in 1 M NaOH (70 mL, 70 mmol). After 1 h stirring at r.t., DCM was added and the layers were separated. The water phase was washed with DCM and the combined organic phases were dried and concentrated to give 6.5 g (98%) of the title compound. 1H NMR: 2.76 (s, 3H) 3.59 (s, 3H) 7.43 (m, 1H) 7.99 (m, 1H) 8.71 (m, 1H) 8.86 (m, 1H)

Workup

  1. customthe layers were separated
  2. washThe water phase was washed with DCM
  3. customthe combined organic phases were dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-454afc4cafe04330ba1f1e96423e8467
Source dataset
uspto-grants-2010_04
Patent number
US07691892B2

Reaction notes

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