Acetic acid, 2-chloro-2-fluoro-, ethyl ester → HCID 54260202, compound

HRID 1382149Notes

Reaction equation

HRID 1382149 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([OH:9])=[CH:4][C:3]=1[N:10]1[C:14](=[O:15])[N:13]([CH:16]([F:18])[F:17])[C:12]([CH3:19])=[N:11]1.Cl[CH:21]([F:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23].[Na]>C(O)C.C(OCC)C>[Cl:8][C:6]1[CH:7]=[C:2]([Cl:1])[C:3]([N:10]2[C:14](=[O:15])[N:13]([CH:16]([F:17])[F:18])[C:12]([CH3:19])=[N:11]2)=[CH:4][C:5]=1[O:9][CH:21]([F:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23]

Participants

6

Reactant 3

HCID 101668Acetic acid, 2-chloro-2-fluoro-, ethyl esterHCID 5360545SodiumHCID 13253747HCID 13253747, compound

Product 1

HCID 54260202HCID 54260202, compoundYield 35.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

To a stirred mixture of 2.0 g (0.0065 mole) of 1-(2,4-dichloro-5-hydroxyphenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one and 0.91 g (0.0065 mole) of ethyl chlorofluoroacetate in 50 mL of ethanol was added a solution of 0.15 g (0.0065 mole) of sodium in 5 mL of ethanol. The reaction mixture was heated at reflux for 34 hours. The mixture was cooled, and the solvent was removed by evaporation under reduced pressure, leaving a residue. This residue was dissolved in diethyl ether, and the solution was washed first with water, followed by an aqueous 10% sodium hydroxide solution. The organic phase was dried over anhydrous magnesium sulfate, then filtered. The filtrate was evaporated under reduced pressure to yield 0.95 g of ethyl [2,4-dichloro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)phenoxy]fluroacetate as an oil, Compound 51.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 34 hours
  3. temperatureThe mixture was cooled
  4. customthe solvent was removed by evaporation under reduced pressure
  5. customleaving a residue
  6. washthe solution was washed first with water
  7. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-a835f0198b834866b0ef1002e91602ab
Source dataset
uspto-grants-1989_02
Patent number
US04806145

Reaction notes

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