Potassium Carbonate → HCID 14392496, compound

HRID 1382151Notes

Reaction equation

HRID 1382151 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]([CH2:16][F:17])[C:12]([CH3:18])=[N:11]1.C(=O)([O-])[O-].[K+].[K+].Br[CH:26]([CH3:32])[C:27]([O:29][CH2:30][CH3:31])=[O:28]>CC(C)=O.CCCCC.[I-].[Na+]>[Cl:8][C:6]1[CH:7]=[C:2]([Cl:1])[C:3]([N:10]2[C:14](=[O:15])[N:13]([CH2:16][F:17])[C:12]([CH3:18])=[N:11]2)=[CH:4][C:5]=1[O:9][CH:26]([CH3:32])[C:27]([O:29][CH2:30][CH3:31])=[O:28]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionateHCID 21274223HCID 21274223, compound

Product 1

HCID 14392496HCID 14392496, compoundYield 93.9%

Reagents, catalysts & solvents 3

HCID 5238Sodium IodideCatalystHCID 180AcetoneSolventHCID 8003PentaneSolvent

Procedure

A mixture of 0.56 g (0.0019 mole) of 1-(2,4-dichloro-5-hydroxyphenyl)-4-fluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one and 1.1 g (0.0076 mole) of anhydrous potassium carbonate in 15 mL of acetone was stirred for 15 minutes. Sodium iodide (approximately 0.01 g) and 0.37 g (0.002 mole) of ethyl 2-bromopropionate were added, and the resultant mixture was heated at reflux for 1.5 hours. The mixture was cooled and filtered. The filtrate was evaporated under reduced pressure, leaving a residue. This residue was partitioned between diethyl ether and water. The organic phase was washed with water, dried over anhydrous magnesium sulfate, and filtered. The filtrate was evaporated under reduced pressure, leaving an oil. This oil was stirred in n-pentane, and the supernant was decanted, leaving an oily residue. The oil was dried at 70° C. under a stream of nitrogen to yield 0.70 g of ethyl 2-[2,4-dichloro-5-(4-fluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)phenoxy]propionate, Compound 13.

Workup

  1. temperatureat reflux for 1.5 hours
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. customThe filtrate was evaporated under reduced pressure
  5. customleaving a residue
  6. customThis residue was partitioned between diethyl ether and water
  7. washThe organic phase was washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customThe filtrate was evaporated under reduced pressure
  11. customleaving an oil
  12. customthe supernant was decanted
  13. customleaving an oily residue
  14. customThe oil was dried at 70° C. under a stream of nitrogen

Sources & evidence

ORD record
ord-58f447b2eba8491abc6bd52b7f54368a
Source dataset
uspto-grants-1989_02
Patent number
US04806145

Reaction notes

Loading…