Benzimidazole → HCID 21465562, compound

HRID 1940003Notes

Reaction equation

HRID 1940003 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=[O:14])[C:8](I)=[CH:9][O:10]2)=[CH:5][CH:4]=1.[N:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[NH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[NH:17][C:16]=1[C:9]1[O:10][C:11]2[C:6]([C:7](=[O:14])[CH:8]=1)=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=2

Participants

5

Reactant 3

HCID 5798BenzimidazoleHCID 11430Potassium CarbonateHCID 8488173-Iodo-7-methoxy-4H-1-benzopyran-4-one

Product 1

HCID 21465562HCID 21465562, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 7-methoxy-3-iodochromone (151 mg) prepared in Example 21, 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 (100.2 mg; yield=68.2%) as white needle crystals. Melting point: 201°-203° C. 1H-NMR(CDCl3, δ ppm): 3.97 (s, 3H, CH3O), 6.52 (br, 1H, H3), 8.17 (d, 1H, H5'), 7.06 (d, 1H, H6), 6.99 (s, 1H, H8), 8.44 (s, 1H, H2'), 7.85 (d, 1H, H4'), 7.46 (m, H5'), 7.46 (m, 1H, H6'), 7.90 (d ,1H, H7').

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-3ac6bae32aa642b2b482926e0cf20e76
Source dataset
uspto-grants-1997_12
Patent number
US05698575

Reaction notes

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