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Ethyl Acetate → 2-(4-Isopropoxy-2-fluorophenyl)-1,2,4-triazine-3,5-dione

HRID 482412
ノート
印刷プレビュー

反応式

HRID 482412 の反応式
[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:16](=[O:17])[NH:15][C:14](=[O:18])[C:13](C(O)=O)=[N:12]2)=[C:7]([F:22])[CH:6]=1)([CH3:3])[CH3:2].C(=O)(O)[O-].[Na+].C(OCC)(=O)C>SCC(O)=O>[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:16](=[O:17])[NH:15][C:14](=[O:18])[CH:13]=[N:12]2)=[C:7]([F:22])[CH:6]=1)([CH3:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 189810712-(4-Isopropoxy-2-fluorophenyl)-1,2,4-triazine-3,5-dion-6-carboxylic acid

生成物 1

HCID 189810222-(4-Isopropoxy-2-fluorophenyl)-1,2,4-triazine-3,5-dione収率 14.9%

試薬・触媒・溶媒 1

HCID 1133Thioglycolic Acid溶媒

実験手順

A solution of 4.70 g (0.0152 mole) of 2-(4-isopropoxy-2-fluorophenyl)-1,2,4-triazine-3,5-dion-6-carboxylic acid in 5 mL of mercaptoacetic acid was heated at 140°-145° C. for two hours under a nitrogen atmosphere. After this mixture had cooled, it was poured into 250 mL of a saturated aqueous solution of sodium bicarbonate with vigorous stirring. An equal volume of ethyl acetate was added to this mixture, and the resulting layers were separated. The organic layer was washed twice with 150 mL of a saturated aqueous solution of sodium bicarbonate and once with 150 mL of a saturated aqueous solution of sodium chloride. The organic solution was then dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure, leaving a syrup which slowly crystallized to a yellow-orange solid upon standing. This solid was recrystallized from ethyl acetate/petroleum ether (1:1), yielding 0.60 g of 2-(4-isopropoxy-2-fluorophenyl)-1,2,4-triazine-3,5-dione as a yellow solid. The NMR was consistent with the proposed structure. This reaction was repeated to obtain additional material for subsequent reactions.

後処理

  1. temperatureAfter this mixture had cooled
  2. customthe resulting layers were separated
  3. washThe organic layer was washed twice with 150 mL of a saturated aqueous solution of sodium bicarbonate and once with 150 mL of a saturated aqueous solution of sodium chloride
  4. dry with materialThe organic solution was then dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was evaporated under reduced pressure
  7. customleaving a syrup which
  8. customslowly crystallized to a yellow-orange solid
  9. customThis solid was recrystallized from ethyl acetate/petroleum ether (1:1)

出典と根拠

ORDレコード
ord-097763e2beb843b8844e8a1885baf987
出典データセット
uspto-grants-1998_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05798316

反応ノート

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