Potassium Iodide → Methyl 5,5,5-trifluoro-4-((4-methoxyphenyl)imino)pent-2-ynoate

HRID 1774282Notes

Reaction equation

HRID 1774282 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3](Cl)=[N:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1.[C:16]([O:20][CH3:21])(=[O:19])[C:17]#[CH:18].P([O-])([O-])([O-])=O.[K+].[K+].[K+].[I-].[K+]>C(#N)C.[Cu]I.O>[F:1][C:2]([F:15])([F:14])[C:3](=[N:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)[C:18]#[C:17][C:16]([O:20][CH3:21])=[O:19]

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 13536Methyl propiolateHCID 62657Potassium Phosphate, TribasicHCID 104216822,2,2-Trifluoro-N-(4-methoxyphenyl)acetimidoyl Chloride

Product 1

HCID 86723348Methyl 5,5,5-trifluoro-4-((4-methoxyphenyl)imino)pent-2-ynoate

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

In a typical reaction, 2,2,2-trifluoro-N-(4-methoxyphenyl)acetimidoyl chloride and a slight excess of methyl propiolate are mixed with about 0.3 equivalents of copper (I) iodide and slight excesses of potassium phosphate and potassium iodide in anhydrous acetonitrile. The mixture is heated at about 60° C. under a nitrogen atmosphere until the reaction is complete. After cooling, an extraction solvent like a halogenated hydrocarbon is added to the mixture along with water. The organic layer is recovered, washed with brine and dried. The solvent is evaporated to provide crude methyl 5,5,5-trifluoro-4-((4-methoxyphenyl)imino)pent-2-ynoate.

Workup

  1. temperatureAfter cooling
  2. customThe organic layer is recovered
  3. washwashed with brine
  4. customdried
  5. customThe solvent is evaporated

Sources & evidence

ORD record
ord-f954cc6e393c4110968471f3da36bf01
Source dataset
uspto-grants-2016_02
Patent number
US09260392B2

Reaction notes

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