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

HRID 1280543Notes

Reaction equation

HRID 1280543 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[NH:11][N:10]=[C:9]([SH:12])[N:8]=2)=[CH:3][CH:2]=1.[CH3:13]C(C)([O-])C.[K+].CI>CN(C=O)C.O>[CH3:13][S:12][C:9]1[N:8]=[C:7]([C:4]2[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=2)[NH:11][N:10]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 178527980HCID 178527980, compound

Product 1

HCID 199148Pyridine, 4-(3-(methylthio)-5(4H)-1,2,4-triazol-5-yl)-Yield 45.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 5-(4-pyridyl)-1H-1,2,4-triazole-3-thiol (Aldrich) (4 g, 22.4 mmol) and .potassium t-butoxide (2.89 g, 25.8 mmol) in DMF (30 mL) was stirred at room temperature under argon until a homogeneous solution resulted. Methyl iodide (1.48 mL 23.8 mmol) was added and the reaction mixture was heated to 50° C. in an oil bath for 16 h. The reaction mixture was diluted with water, extracted with EtOAc, the organic extract was washed with water and dried (MgSO4). The solid obtained on concentration was filtered from hot ethyl acetate to obtain 3-methylthio-5-(4-pyridyl)-1H-1,2,4-triazole (1.97 g).

Workup

  1. customresulted
  2. extractionextracted with EtOAc
  3. extractionthe organic extract
  4. washwas washed with water
  5. dry with materialdried (MgSO4)
  6. customThe solid obtained on concentration
  7. filtrationwas filtered from hot ethyl acetate

Sources & evidence

ORD record
ord-6956a0e8e24c40d1843d7f6cdc02ef44
Source dataset
uspto-grants-2002_09
Patent number
US06451820B1

Reaction notes

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