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

HRID 35422Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 35422
[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

Komponenten

6

Edukt 3

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

Produkt 1

HCID 142769432-[2,4-dichloro-5-(1-methylethoxy)phenyl]-6-methyl-1,2,4-triazine-3,5(2H,4H)-dioneAusbeute 58,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1118Sulfuric AcidKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-61e5df5ed54e45239fddd602ea4f2845
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04766233

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