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

HRID 1488417ノート

反応式

HRID 1488417 の反応式
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

参加物

3

反応物 2

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

生成物 1

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

反応条件

温度
0 °C

実験手順

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 9° 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.

後処理

  1. temperatureThe mixture was maintained at 9° 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

出典と根拠

ORDレコード
ord-166d331ecbea49ed972a701a5b42cd0d
出典データセット
uspto-grants-1997_10
特許番号
US05674810

反応ノート

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