Potassium Iodide → HCID 68488284, compound

HRID 1470867Notes

Reaction equation

HRID 1470867 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.N[C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH3:27])=[C:22]([CH:28]3[C:33](=[O:34])[C:32]([CH3:36])([CH3:35])[O:31][C:30]([CH3:38])([CH3:37])[C:29]3=[O:39])[CH:21]=2)=[CH:16][CH:15]=1.N([O-])=O.[Na+].[I-:44].[K+].C(=O)(O)[O-].[Na+]>C(#N)C.O.C(OCC)(=O)C>[I:44][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH3:27])=[C:22]([CH:28]3[C:33](=[O:34])[C:32]([CH3:36])([CH3:35])[O:31][C:30]([CH3:38])([CH3:37])[C:29]3=[O:39])[CH:21]=2)=[CH:16][CH:15]=1

Participants

9

Reactant 5

HCID 4875Potassium IodideHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 23668193Sodium NitriteHCID 68481510HCID 68481510, compound

Product 1

HCID 68488284HCID 68488284, compoundYield 48.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of para-toluenesulfonic acid monohydrate (1.03 g, 5.40 mmol) in acetonitrile (11 ml) is added 4-(4′-amino-4-ethylbiphenyl-3-yl)-2,2,6,6-tetramethyl-pyran-3,5-dione (0.65 g, 1.80 mmol), followed by stirring for 10 minutes at room temperature then cooling to 10° C. To this mixture is then added a second mixed solution of sodium nitrite (0.25 g, 3.60 mmol) and potassium iodide (0.76 g, 4.50 mmol) in distilled water (1.3 ml), and the mixture is then stirred at 10° C. for 20 minutes then at room temperature for 2 hours. Aqueous sodium bicarbonate solution is added until pH 9-10 is achieved, followed by dilution with ethyl acetate and washing with saturated aqueous sodium metabisulfite (20 ml). After additional extraction of the aqueous phase using ethyl acetate (×2) all organic fractions are combined, washed with distilled water and brine, then dried over anhydrous magnesium sulfate and concentrated in vacuo. This crude product is purified by flash column chromatography on silica gel (hexane/ethyl acetate 3:1 ratio) to yield an orange gum, which is triturated with hexanes to afford 4-(4′-iodo-4-ethylbiphenyl-3-yl)-2,2,6,6-tetramethylpyran-3,5-dione (0.413 g) as a white solid.

Workup

  1. temperaturethen cooling to 10° C
  2. stirringthe mixture is then stirred at 10° C. for 20 minutes
  3. waitat room temperature for 2 hours
  4. washwashing with saturated aqueous sodium metabisulfite (20 ml)
  5. extractionAfter additional extraction of the aqueous phase
  6. washwashed with distilled water and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customThis crude product is purified by flash column chromatography on silica gel (hexane/ethyl acetate 3:1 ratio)
  10. customto yield an orange gum, which
  11. customis triturated with hexanes

Sources & evidence

ORD record
ord-b6e7855fea674fa8b5762785490153f9
Source dataset
uspto-grants-2015_04
Patent number
US09006429B2

Reaction notes

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