Cesium carbonate → 1,4-Bis(4-methoxyphenyl)-1H-imidazole

HRID 1428939Notes

Reaction equation

HRID 1428939 reaction equation
[I-].[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[CH:12][NH:13][CH:14]=2)=[CH:6][CH:5]=1.I[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[CH3:23][O:22][C:19]1[CH:20]=[CH:21][C:16]([N:13]2[CH:14]=[C:10]([C:7]3[CH:8]=[CH:9][C:4]([O:3][CH3:2])=[CH:5][CH:6]=3)[N:11]=[CH:12]2)=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 30165Iodide IonHCID 696764-IodoanisoleHCID 178418716HCID 178418716, compound

Product 1

HCID 581572311,4-Bis(4-methoxyphenyl)-1H-imidazoleYield 56.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

10 mg cupper (I) iodide, 20 mg trans-N,N′-dimethyl-1,2-cyclohexyldiamine was added to 1.1 g 4-(4-methoxy-phenyl)-1H-imidazole, 1.5 g 1-iodo-4-methoxy-benzene and 1.95 g cesium carbonate in 5 mL DMF under argon. The reaction was stirred 48 h at 120° C. in a closed microwave bottle under argon. Water was added and the reaction was extracted with ethyl acetate. The organic layer was dried and evaporated. The residue was purified by chromatography on Alox (50 kg, Merck (Darmstadt), Bestell-Nr. 1.01097.9050 activity: II-III) (gradient: dichlormethane/EtOAC 9:1-8:2) to yield 1 g of the desired compound.

Workup

  1. extractionthe reaction was extracted with ethyl acetate
  2. customThe organic layer was dried
  3. customevaporated
  4. customThe residue was purified by chromatography on Alox (50 kg, Merck (Darmstadt), Bestell-Nr. 1.01097.9050 activity: II-III) (gradient: dichlormethane/EtOAC 9:1-8:2)

Sources & evidence

ORD record
ord-b81a108b1ffa41458a66d8c4be733565
Source dataset
uspto-grants-2015_01
Patent number
US08937176B2

Reaction notes

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