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

HRID 1650696Notes

Reaction equation

HRID 1650696 reaction equation
[SH:1][C:2]1[N:6]=[C:5]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)[NH:4][N:3]=1.[OH-].[K+].[CH3:15]I>O.CCOCC.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:15][S:1][C:2]1[N:6]=[C:5]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)[NH:4][N:3]=1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 178527979HCID 178527979, compound

Product 1

HCID 196124903-[3-(Methylsulfanyl)-1H-1,2,4-triazol-5-yl]pyridine

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 20 g (0.100 mol) of 65 and 7.5 g (0.150 mol) of potassium hydroxide in 100 ml of water was mixed with a solution of 10 ml (0.160 mol) of methyl iodide in 100 ml of ether. After addition of 1 g of tetrabutylammonium hydrogen sulphate the mixture was stirred overnight at room temperature. The ether phase was separated and the aqueous phase extracted with 3×100 ml of ether. The combined organic phases were dried over magnesium sulphate. Removal of the solvent in vacuo gave a colorless solid, 66. Yield: 17.0 g (0.089 mol, 89%).

Workup

  1. customThe ether phase was separated
  2. extractionthe aqueous phase extracted with 3×100 ml of ether
  3. dry with materialThe combined organic phases were dried over magnesium sulphate
  4. customRemoval of the solvent in vacuo
  5. customgave a colorless solid, 66

Sources & evidence

ORD record
ord-475e8b2a29274c30ade06e448936762f
Source dataset
uspto-grants-1990_05
Patent number
US04925858

Reaction notes

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