8-Hydroxyquinoline → HCID 66974213, compound

HRID 499836Notes

Reaction equation

HRID 499836 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][CH:3]=1.[CH3:9][S:10][C:11]1[NH:12][CH:13]=[C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:15]=1.OC1C=CC=C2C=1N=CC=C2.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.[Cu]I.CCOC(C)=O.O>[I:8][C:5]1[CH:6]=[CH:7][C:2]([N:12]2[CH:13]=[C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:15]=[C:11]2[S:10][CH3:9])=[CH:3][CH:4]=1

Participants

9

Reactant 4

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 12208p-DiiodobenzeneHCID 178469908HCID 178469908, compound

Product 1

HCID 66974213HCID 66974213, compoundYield 10.4%

Reagents, catalysts & solvents 4

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

Conditions

Temperature
130 °C

Procedure

A mixture of 1,4-diiodobenzene 1-1 (4.00 g, 12.1 mmol), ethyl 2-(methylthio)-1H-imidazole-4-carboxylate (2.26 g, 12.1 mmol), 8-hydroxyquinoline (270 mg, 1.86 mmol) and K2CO3 (3.40 g, 24.6 mmol) in DMSO (12 mL) was degassed with Ar before being charged with CuI (345 mg, 1.82 mmol). The mixture in a sealed tube was heated at 130° C. for 3 days. After cooling down, H2O and EtOAc were added. After being filtered through celite, the organic phase was separated, dried over Na2SO4, concentrated in vacuo. The residue was purified by a silica gel column, eluted with EtOAc in hexane (10-35% EtOAc) to give ethyl 1-(4-iodophenyl)-2-(methylthio)-1H-imidazole-4-carboxylate (0.49 g).

Workup

  1. customwas degassed with Ar
  2. temperatureAfter cooling down
  3. filtrationAfter being filtered through celite
  4. customthe organic phase was separated
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by a silica gel column
  8. washeluted with EtOAc in hexane (10-35% EtOAc)

Sources & evidence

ORD record
ord-038732f38cbf4b13ba5892c5da195b29
Source dataset
uspto-grants-2010_08
Patent number
US07767697B2

Reaction notes

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