Methyl iodide → 3-Benzyl-4-(2,2-diethoxyethyl)-5-methylthio-1,2,4-triazole

HRID 26494Notes

Reaction equation

HRID 26494 reaction equation
[CH2:1]([C:8]1[N:12]([CH2:13][CH:14]([O:18][CH2:19][CH3:20])[O:15][CH2:16][CH3:17])[C:11](=[S:21])[NH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:22][O-].[Na+].CI>CO>[CH2:1]([C:8]1[N:12]([CH2:13][CH:14]([O:18][CH2:19][CH3:20])[O:15][CH2:16][CH3:17])[C:11]([S:21][CH3:22])=[N:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10942334Sodium MethoxideHCID 213233313-benzyl-4-(2,2-diethoxyethyl)-4H-1,2,4-triazole-5-thione

Product 1

HCID 213234073-Benzyl-4-(2,2-diethoxyethyl)-5-methylthio-1,2,4-triazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

In 3 ml of methanol was dissolved 0.307 g of the 3-benzyl-4-(2,2-diethoxyethyl)-4H-1,2,4-triazole-5-thione prepared in Reference Example 2, followed by addition of 0.6 ml of a 2N solution of sodium methoxide in methanol. Under stirring, 0.07 ml of methyl iodide was added dropwise and, after 30 minutes, the methanol was evaporated off. The residue was diluted with water and extracted with chloroform. The chloroform layer was washed with water, dried over Na2SO4. Evaporation of the solvent gave 3-benzyl-4-(2,2-diethoxyethyl)-5-methylthio-4H-1,2,4-triazole as an oil (quantitative yield).

Workup

  1. customprepared in Reference Example 2
  2. customthe methanol was evaporated off
  3. additionThe residue was diluted with water
  4. extractionextracted with chloroform
  5. washThe chloroform layer was washed with water
  6. dry with materialdried over Na2SO4
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-1671ce6a0fd34a36a5561294eea699a4
Source dataset
uspto-grants-1979_04
Patent number
US04150139

Reaction notes

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