Water → 2-[2,4-dichloro-5-(1-methylethoxy)phenyl]-6-methyl-1,2,4-triazine-3,5(2H,4H)-dione

HRID 1164752Notes

Reaction equation

HRID 1164752 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:10]([CH3:12])[CH3:11])=[CH:4][C:3]=1[N:13]1[C:17](=[O:18])[NH:16][C:15]([CH3:20])([CH3:19])[NH:14]1.C(O)(=O)C(C)=[O:23].O>O1CCOCC1.S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:10]([CH3:12])[CH3:11])=[CH:4][C:3]=1[N:13]1[C:17](=[O:18])[NH:16][C:19](=[O:23])[C:15]([CH3:20])=[N:14]1

Participants

6

Reactant 3

HCID 962WaterHCID 1060Pyruvic Acid2×HCID 147478291-[2,4-Dichloro-5-(1-methylethoxy)phenyl]-3,3-dimethyl-1,2,4-triazolidin-5-one

Product 1

HCID 142769432-[2,4-dichloro-5-(1-methylethoxy)phenyl]-6-methyl-1,2,4-triazine-3,5(2H,4H)-dioneYield 58.6%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a stirred mixture of 1.0 g (0.0031 mole) of 1-[2,4-dichloro-5-(1-methylethoxy)phenyl]-3,3-dimethyl-1,2,4-triazolidin-5-one in 10 mL of p-dioxane was added 0.29 g (0.0031 mole) of pyruvic acid and one drop of concentrated sulfuric acid. The mixture was stirred at room temperature for one hour, then an additional 0.25 g (0.0029 mole) of pyruvic acid was added. The mixture was heated at 90° C. for three hours, then poured into water. The mixture was extracted with ethyl acetate, and the solvent was evaporated from the extract under reduced pressure to give an oil. The oil was purified by thin-layer preparative chromatography on silica gel, eluting with ethyl acetate:heptane (1:1). Extraction of the appropriate bands gave 0.6 g of 2-[2,4-dichloro-5-(1-methylethoxy)phenyl]-6-methyl-1,2,4-triazine-3,5(2H,4H)-dione as a solid (mp 163°-164° C.), Compound 10 in the tables.

Workup

  1. temperatureThe mixture was heated at 90° C. for three hours
  2. extractionThe mixture was extracted with ethyl acetate
  3. customthe solvent was evaporated from the
  4. extractionextract under reduced pressure
  5. customto give an oil
  6. customThe oil was purified by thin-layer preparative chromatography on silica gel
  7. washeluting with ethyl acetate:heptane (1:1)
  8. extractionExtraction of the appropriate bands

Sources & evidence

ORD record
ord-3c56162d2a434620b7ff23639ab7645b
Source dataset
uspto-grants-1990_03
Patent number
US04906286

Reaction notes

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