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

HRID 2225406
Notes
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Reaction equation

HRID 2225406 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1133Thioglycolic AcidSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-a342c2ebad14478393a37f043e548e23
Source dataset
uspto-grants-1994_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05344812

Reaction notes

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