Picolinic acid → 2,2'-(oxybis(3,1-phenylene))bis(1-phenyl-1H-imidazole)

HRID 539485Notes

Reaction equation

HRID 539485 reaction equation
[C:1]1([N:7]2[CH:11]=[CH:10][N:9]=[C:8]2[C:12]2[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I[C:20]1[CH:21]=[C:22]([C:26]2[N:27]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:28]=[CH:29][N:30]=2)[CH:23]=[CH:24][CH:25]=1.N1C=CC=CC=1C(O)=O.O.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C(OCC)(=O)C.O.[Cu]I.CS(C)=O>[O:18]([C:24]1[CH:23]=[C:22]([C:26]2[N:27]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:28]=[CH:29][N:30]=2)[CH:21]=[CH:20][CH:25]=1)[C:14]1[CH:13]=[C:12]([C:8]2[N:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:11]=[CH:10][N:9]=2)[CH:17]=[CH:16][CH:15]=1

Participants

9

Reactant 4

HCID 1018Picolinic acidHCID 22031701Potassium phosphate, tribasic, monohydrateHCID 706543922-(3-iodophenyl)-1-phenyl-1H-imidazoleHCID 706545343-(1-phenyl-1H-imidazol-2-yl)phenol

Product 1

HCID 706542762,2'-(oxybis(3,1-phenylene))bis(1-phenyl-1H-imidazole)Yield 43.1%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
200 °C

Procedure

To a 500 mL 3-neck round bottom flask was added 3-(1-phenyl-1H-imidazol-2-yl)phenol (3.05 g, 12.26 mmol), 2-(3-iodophenyl)-1-phenyl-1H-imidazole (4.67 g, 13.49 mmol), picolinic acid (2.27 g, 18.40 mmol), copper(I) iodide (0.70 g, 3.68 mmol), potassium phosphate tribasic monohydrate (9.88 g, 42.9 mmol), and 200 mL DMSO. Nitrogen was bubbled directly into the mixture and was heated to 200° C. for 3 h and then at 120° C. overnight under nitrogen. The cooled reaction mixture was diluted with ethyl acetate and water. The mixture was filtered through Celite® and the Celite® was washed with ethyl acetate and water. The layers were separated and the aqueous layer was extracted with ethyl acetate. The organic layers were washed with brine, dried over magnesium sulfate, filtered, and evaporated. The residue was purified by column chromatography eluting with ethyl acetate to give pure product (2.4 g, 43%).

Workup

  1. customNitrogen was bubbled directly into the mixture
  2. customat 120° C.
  3. customovernight
  4. customThe cooled reaction mixture
  5. filtrationThe mixture was filtered through Celite®
  6. washthe Celite® was washed with ethyl acetate and water
  7. customThe layers were separated
  8. extractionthe aqueous layer was extracted with ethyl acetate
  9. washThe organic layers were washed with brine
  10. dry with materialdried over magnesium sulfate
  11. filtrationfiltered
  12. customevaporated
  13. customThe residue was purified by column chromatography
  14. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-05aaedbcf312436c8eeccc48358bcf9d
Source dataset
uspto-grants-2014_10
Patent number
US08871361B2

Reaction notes

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