Sulfuric Acid → 2-(4-Hydroxy-2-fluorophenyl)-4-methyl-1,2,4-triazine-3,5-dione

HRID 482414Notes

Reaction equation

HRID 482414 reaction equation
S(=O)(=O)(O)O.C([O:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[C:21](=[O:22])[N:20]([CH3:23])[C:19](=[O:24])[CH:18]=[N:17]2)=[C:12]([F:25])[CH:11]=1)(C)C>>[OH:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[C:21](=[O:22])[N:20]([CH3:23])[C:19](=[O:24])[CH:18]=[N:17]2)=[C:12]([F:25])[CH:11]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 189810722-(4-Isopropoxy-2-fluorophenyl)-4-methyl-1,2,4-triazine-3,5-dione

Product 1

HCID 189810672-(4-Hydroxy-2-fluorophenyl)-4-methyl-1,2,4-triazine-3,5-dione

Conditions

Temperature
0 °C

Procedure

Concentrated sulfuric acid (5 mL) that had been cooled to 0°-5° C. was mixed with 2.80 g (0.010 mole) of 2-(4-isopropoxy-2-fluorophenyl)-4-methyl-1,2,4-triazine-3,5-dione that had been cooled to 0° C. The mixture was maintained at 0° C. for ten minutes, during which time it became homogeneous. The mixture was then poured into ice-water, and the resulting mixture was extracted with ethyl acetate. The extract was washed in succession with a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride. The extract was dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated from the filtrate under reduced pressure, leaving a residue. This residue was placed on a column of silica gel and eluted with ethyl acetate/hexane (1:1). After the product-containing fractions were combined and the solvents evaporated under reduced pressure, 1.38 g of 2-(4-hydroxy-2-fluorophenyl)-4-methyl-1,2,4-triazine-3,5-dione was recovered as a stiff syrup. The NMR was consistent with the proposed structure.

Workup

  1. temperatureThe mixture was maintained at 0° C. for ten minutes, during which time it
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe extract was washed in succession with a saturated aqueous solution of sodium bicarbonate
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was evaporated from the filtrate under reduced pressure
  7. customleaving a residue
  8. washeluted with ethyl acetate/hexane (1:1)
  9. customthe solvents evaporated under reduced pressure, 1.38 g of 2-(4-hydroxy-2-fluorophenyl)-4-methyl-1,2,4-triazine-3,5-dione
  10. customwas recovered as a stiff syrup

Sources & evidence

ORD record
ord-81dc6b7016e24da593f7006ac30f7449
Source dataset
uspto-grants-1998_08
Patent number
US05798316

Reaction notes

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