Sodium Methoxide → 2,4-dihydro-5-methoxy-2-methyl-4-(2-methylphenyl)-3H-1,2,4-triazol-3-one

HRID 376845Notes

Reaction equation

HRID 376845 reaction equation
Cl[C:2]1[N:3]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])[C:4](=[O:8])[N:5]([CH3:7])[N:6]=1.[CH3:16][O-:17].[Na+]>C(COC)OC.CO.C(OCC)(=O)C>[CH3:16][O:17][C:2]1[N:3]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])[C:4](=[O:8])[N:5]([CH3:7])[N:6]=1

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 187898205-Chloro-2-methyl-4-(o-tolyl)-2,4-dihydro[1,2,4]triazol-3-one

Product 1

HCID 187898082,4-dihydro-5-methoxy-2-methyl-4-(2-methylphenyl)-3H-1,2,4-triazol-3-oneYield 95%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 86595564Dimethoxyethane methanolSolvent

Procedure

8.25 g 5-chloro-2,4-dihydro-2-methyl-4-(2-methylphenyl)-3H-1,2,4-triazol-3-one was dissolved in 80 mL 1:1 dimethoxyethane/methanol under N2. 14.0 mL sodium methoxide (30% solution in methanol) was added and the solution was heated at reflux for 3 h. The mixture was allowed to cool, diluted with ethyl acetate, washed with water, then saturated aqueous NaCl. The combined organic extracts were dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography (50-70% ethyl acetate/hexanes as eluent) and triturated with 50% diethylether/hexanes to afford 6.7 g of the title compound of Step C (95% pure). 1H NMR (CDCl3) δ 7.35-7.27 (m,3H), 7.18 (d,1H), 3.94 (s,3H), 3.46 (s,3H), 2.22 (s,3H).

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux for 3 h
  3. temperatureto cool
  4. washwashed with water
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash chromatography (50-70% ethyl acetate/hexanes as eluent)
  9. customtriturated with 50% diethylether/hexanes

Sources & evidence

ORD record
ord-85c82b0811ba4c1290f3f9c4f315c029
Source dataset
uspto-grants-2000_02
Patent number
US06022870

Reaction notes

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