Benzimidazole → 2-Benzimidazolyl-6-chlorochromone

HRID 1940005Notes

Reaction equation

HRID 1940005 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]=[C:6](I)[C:5]2=[O:13].[N:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[NH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[NH:16][C:15]=1[C:7]1[O:8][C:9]2[C:4]([C:5](=[O:13])[CH:6]=1)=[CH:3][C:2]([Cl:1])=[CH:11][CH:10]=2

Participants

5

Reactant 3

HCID 5798BenzimidazoleHCID 11430Potassium CarbonateHCID 116666776-Chloro-3-iodochromone

Product 1

HCID 214655762-Benzimidazolyl-6-chlorochromoneYield 13%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-chloro-3-iodochromone (153 mg) prepared in Example 28, benzimidazole (236 mg), potassium carbonate (1382 mg), and dimethylformamide (15 ml) was reacted at 80° C. for 2 hours with stirring. The reaction mixture was added to ice water and extracted from chloroform. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purifiedby the silica gel column chromatography, and recrystallized from benzene/hexane to give the titled compound (19.3 mg; yield=13.0%) as white crystals. Melting point: 248°-250° C. Mass spectrum (M+): 296.5.

Workup

  1. customwas reacted at 80° C. for 2 hours
  2. extractionextracted from chloroform
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customrecrystallized from benzene/hexane

Sources & evidence

ORD record
ord-6d326ea2b48e49fdb6b9c75e35a9aae7
Source dataset
uspto-grants-1997_12
Patent number
US05698575

Reaction notes

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