Sodium hydride → HCID 13822256, compound

HRID 1382137Notes

Reaction equation

HRID 1382137 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([N:9]2[C:13](=[O:14])[N:12]([CH:15]([F:17])[F:16])[C:11]([CH3:18])=[N:10]2)=[C:4]([F:19])[CH:3]=1.[H-].[Na+].Br[CH:23]([CH3:28])[C:24]([O:26][CH3:27])=[O:25]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([F:19])[C:5]([N:9]2[C:13](=[O:14])[N:12]([CH:15]([F:16])[F:17])[C:11]([CH3:18])=[N:10]2)=[CH:6][C:7]=1[O:8][CH:23]([CH3:28])[C:24]([O:26][CH3:27])=[O:25]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 95576Methyl 2-bromopropionateHCID 137694562-(4-Chloro-2-fluoro-5-hydroxyphenyl)-4-(difluoromethyl)-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one

Product 1

HCID 13822256HCID 13822256, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 1.5 g (0.0051 mole) of 1-(4-chloro-2-fluoro-5-hydroxyphenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one and 0.12 g (0.0051 mole) of sodium hydride in 50 mL of N,N-dimethylformamide was added 0.85 g (0.0051 mole) of methyl 2-bromopropionate. After complete addition the reaction mixture was heated at reflux for two hours, then cooled to room temperature and stirred for approximately 18 hours. The solvent was removed by evaporation under reduced pressure leaving a residue. This residue was partitioned between diethyl ether and water. The organic phase was washed with an aqueous 10% sodium hydroxide solution. The organic phase was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure to yield 1.5 g of methyl 2-[2-chloro-4-fluoro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)phenoxy]propionate as an oil, Compound 3.

Workup

  1. additionAfter complete addition the reaction mixture
  2. temperaturewas heated
  3. temperatureat reflux for two hours
  4. customThe solvent was removed by evaporation under reduced pressure
  5. customleaving a residue
  6. customThis residue was partitioned between diethyl ether and water
  7. washThe organic phase was washed with an aqueous 10% sodium hydroxide solution
  8. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-cb8ace7f33214905a9ed690a5b99497e
Source dataset
uspto-grants-1989_02
Patent number
US04806145

Reaction notes

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