Ethyl Acetate → PS-13

HRID 584742Notes

Reaction equation

HRID 584742 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:19]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)=[N:18][C:17]([OH:28])=[N:16]2)=[CH:11][CH:10]=1.[F:29][C:30]([F:34])([F:33])[CH2:31]I.C(OCC)(=O)C>CN(C)C=O.O>[CH3:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([N:15]2[C:19]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)=[N:18][C:17]([O:28][CH2:31][C:30]([F:34])([F:33])[F:29])=[N:16]2)=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 677091,1,1-Trifluoro-2-iodoethaneHCID 1784890151,5-bis(4-methoxyphenyl)-1H-1,2,4-triazol-3-ol

Product 1

HCID 22341583PS-13Yield 53.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Potassium carbonate (697 mg, 5.05 mmol) was added to a solution of 1,5-bis(4-methoxyphenyl)-1H-1,2,4-triazol-3-ol (0.3 g, 1.01 mmol) in dimethylformamide (3 mL). After 10 minute stirring, 2,2,2-trifluoroethyl iodide (0.497 mL, 5.05 mmol) was added to the mixture and the mixture was heated at 100° C. for 3 hours. After cooling, 100 mL of ethyl acetate and 20 mL of water were poured into the mixture. The organic layer was separated, washed with water and brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate 10:1-5:1). The desired product was triturated with hexane, isolated by filtartion, and dried in vacuo to give 1,5-bis(4-methoxyphenyl)-3-(2,2,2-trifluoroethoxy)-1H-1,2,4-triazole (205 mg, 53.6%).

Workup

  1. temperatureAfter cooling
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate 10:1-5:1)
  7. customThe desired product was triturated with hexane
  8. customisolated by filtartion
  9. customdried in vacuo

Sources & evidence

ORD record
ord-4b19f922d20448afb25ffa7d03fe0d55
Source dataset
uspto-grants-2005_08
Patent number
US06927230B2

Reaction notes

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