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

HRID 1453805Notes

Reaction equation

HRID 1453805 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)=[N:5][NH:4][C:3]1=[S:13].[CH3:14]I.[OH-].[Na+].O>CC(C)=O>[CH3:1][N:2]1[C:3]([S:13][CH3:14])=[N:4][N:5]=[C:6]1[C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 7385474-methyl-5-(pyridin-4-yl)-4H-1,2,4-triazole-3-thiol

Product 1

HCID 8659874-(4-Methyl-5-(methylthio)-4H-1,2,4-triazol-3-yl)pyridineYield 82%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mechanically stirred and cooled (9° C.) suspension of 4-methyl-5-pyridin-4-yl-2,4-dihydro-3H-1,2,4-triazole-3-thione (267 g) and methyl iodide (197.7 g) in acetone (2.6 L), was added a solution of sodium hydroxide (54 g in 600 mL of water) at such a rate (ca. 20 mL/min) as to maintain the temperature between 10 and 15° C. Another portion of water (50 mL) was then added and the temperature was allowed to come to 21 to 24° C. After another 2 h, the acetone was distilled off from the reaction mixture in vacuo (water-bath kept at 30° C.). Another portion of water (750 mL) was then added before cooling (17 to 18° C.) and collection of the formed precipitate by filtration. This solid was then washed with water (2×1 L) before drying at 100 mbar under a gentle stream of air for 3 days to yield 235 g of the title compound as a white powder. 1H NMR (DMSO-d6): 2.7 (s, 3H), 3.6 (s, 3H), 7.7 (m, 2H), 8.8 (d, 2H).

Workup

  1. temperaturecooled
  2. temperatureto maintain the temperature between 10 and 15° C
  3. customto come to 21 to 24° C
  4. distillationthe acetone was distilled off from the reaction mixture in vacuo (water-bath kept at 30° C.)
  5. additionAnother portion of water (750 mL) was then added
  6. temperaturebefore cooling
  7. custom(17 to 18° C.) and collection of the formed precipitate
  8. filtrationby filtration
  9. washThis solid was then washed with water (2×1 L)
  10. custombefore drying at 100 mbar under a gentle stream of air for 3 days

Sources & evidence

ORD record
ord-5b7a7d1f6ca74994983317c6f5f702d9
Source dataset
uspto-grants-2009_01
Patent number
US07476684B2

Reaction notes

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