Hydrochloric Acid → 2-(4-Isopropoxy-2-fluorophenyl)-4-methyl-1,2,4-triazine-3,5-dione

HRID 257381Notes

Reaction equation

HRID 257381 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])[CH:13]=[N:12]2)=[C:7]([F:19])[CH:6]=1)([CH3:3])[CH3:2].[H-].[Na+].I[CH3:23].Cl>CN(C)C=O>[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:16](=[O:17])[N:15]([CH3:23])[C:14](=[O:18])[CH:13]=[N:12]2)=[C:7]([F:19])[CH:6]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 189810222-(4-Isopropoxy-2-fluorophenyl)-1,2,4-triazine-3,5-dione

Product 1

HCID 189810722-(4-Isopropoxy-2-fluorophenyl)-4-methyl-1,2,4-triazine-3,5-dioneYield 81.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 3.25 g (0.0123 mole) of 2-(4-isopropoxy-2-fluorophenyl)-1,2,4-triazine-3,5-dione in 30 mL of N,N-dimethylformamide was added to a suspension of 0.50 g (0.0125 mole) of sodium hydride in 30 mL of N,N-dimethylformamide at ambient temperature. When gas evolution had ceased, 3.55 g (0.025 mole) of iodomethane was added in one portion. This mixture was stirred for one hour without heating and was then poured into 300 mL of dilute hydrochloric acid. The resulting mixture was extracted several times with diethyl ether, and the extracts were combined. The ether extract was washed in succession with water and a saturated aqueous solution of sodium chloride. It was then dried over anhydrous magnesium sulfate and filtered through a short column of silica gel. The solvent was evaporated under reduced pressure, leaving 2.80 g of 2-(4-isopropoxy-2-fluorophenyl)-4-methyl-1,2,4-triazine-3,5-dione as a syrup. The NMR was consistent with the proposed structure.

Workup

  1. temperaturewithout heating
  2. extractionThe resulting mixture was extracted several times with diethyl ether
  3. extractionThe ether extract
  4. washwas washed in succession with water
  5. dry with materialIt was then dried over anhydrous magnesium sulfate
  6. filtrationfiltered through a short column of silica gel
  7. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b7a79282bdfa46638a89ea2f999b505f
Source dataset
uspto-grants-1993_11
Patent number
US05262390

Reaction notes

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