Methanol → 1-(4-methoxyphenyl)-3-(methylthio)-1H-1,2,4-triazole

HRID 971673Notes

Reaction equation

HRID 971673 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:13]=[N:12][C:11]([SH:14])=[N:10]2)=[CH:5][CH:4]=1.[OH-].[Na+].CO.S(OC)(O[CH3:23])(=O)=O>O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH:13]=[N:12][C:11]([S:14][CH3:23])=[N:10]2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 178492027HCID 178492027, compound

Product 1

HCID 130198981-(4-methoxyphenyl)-3-(methylthio)-1H-1,2,4-triazoleYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 8 parts of 1-(4-methoxyphenyl)-1H-1,2,4-triazole-3-thiol, 3.1 parts of sodium hydroxide and 40 parts of methanol is stirred for 30 minutes at room temperature. Then there are added 4.9 parts of dimethyl sulfate and stirring at room temperature is continued for 3 hours. Water is added to the reaction mixture and the product is extracted twice with 1,1'-oxybisethane. The combined extracts are dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using trichloromethane as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from 2,2'-oxybispropane, yielding 5.6 parts (65%) of 1-(4-methoxyphenyl)-3-(methylthio)-1H-1,2,4-triazole; mp. 54.9° C.

Workup

  1. stirringstirring at room temperature
  2. waitis continued for 3 hours
  3. extractionthe product is extracted twice with 1,1'-oxybisethane
  4. customThe combined extracts are dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified by column-chromatography over silica gel
  8. customThe pure fractions are collected
  9. customthe eluent is evaporated
  10. customThe residue is crystallized from 2,2'-oxybispropane

Sources & evidence

ORD record
ord-1122c9d82f904949a65e3b83462409f7
Source dataset
uspto-grants-1979_07
Patent number
US04160841

Reaction notes

Loading…