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

HRID 1106705Notes

Reaction equation

HRID 1106705 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 of the title compound of Step B was dissolved in 80 mL of 1:1 dimethoxyethane/methanol under N2. 14.0 mL of 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, and then washed with 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% diethyl etherlhexanes 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), 2.2 (s,3H).

Workup

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

Sources & evidence

ORD record
ord-be4dbe82d02c461c81a959ed79b93335
Source dataset
uspto-grants-2000_05
Patent number
US06057352

Reaction notes

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