Potassium Iodide → HCID 86723378, compound

HRID 508538Notes

Reaction equation

HRID 508538 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3](Cl)=[N:4][C:5]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH2:27]([O:29][CH:30]([O:33][CH2:34][CH3:35])[C:31]#[CH:32])[CH3:28].P([O-])([O-])([O-])=O.[K+].[K+].[K+].[I-].[K+]>C(#N)C.[Cu]I.O>[CH2:27]([O:29][CH:30]([O:33][CH2:34][CH3:35])[C:31]#[C:32][C:3](=[N:4][C:5]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:2]([F:26])([F:25])[F:1])[CH3:28]

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 62657Potassium Phosphate, TribasicHCID 662853,3-DiethoxypropyneHCID 86723377HCID 86723377, compound

Product 1

HCID 86723378HCID 86723378, compound

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-(trityl)ethanimidoyl chloride and a slight excess of 3,3-diethoxyprop-1-yne 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 N-(5,5-diethoxy-1,1,1-trifluoropent-3-yn-2-ylidene)-1,1,1-triphenylmethanamine.

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-9fb1846c13e04724bbaac19a59b79f26
Source dataset
uspto-grants-2015_08
Patent number
US09096526B2

Reaction notes

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