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

HRID 1488417노트

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HRID 1488417 반응식
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

참가 물질

3

반응물 2

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

생성물 1

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

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-166d331ecbea49ed972a701a5b42cd0d
출처 데이터셋
uspto-grants-1997_10
특허 번호
US05674810

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