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

HRID 904003Notes

Reaction equation

HRID 904003 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-dcd663eb76d94b2eac561e7ca84e9102
Source dataset
uspto-grants-1980_10
Patent number
US04229581

Reaction notes

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