Benzimidazole → HCID 9797221, compound

HRID 1939999Notes

Reaction equation

HRID 1939999 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[C:5](=[O:16])[C:6](I)=[CH:7][O:8]2.[N:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[NH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[NH:19][C:18]=1[C:7]1[O:8][C:9]2[C:4]([C:5](=[O:16])[CH:6]=1)=[C:3]([O:2][CH3:1])[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=2

Participants

5

Reactant 3

HCID 5798BenzimidazoleHCID 11430Potassium CarbonateHCID 21465560HCID 21465560, compound

Product 1

HCID 9797221HCID 9797221, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5,7-dimethoxy-3-iodochromone (166 mg) prepared in Example 16, 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 (107.9 mg; yield =67.0%) as orange plate crystals. Melting point: 245°-246° C. Mass spectrum (M+): 332. 1H-NMR(CDCl3, δ ppm): 6.71 (s, 1H, H3), 6.62 (s, H6), 8.26 (s, H8), 6.43 (s, H3'), 7.80 (d, H4'), 7.58 (t, H5'), 7.34 (t, H6'), 8.11 (d, H7'), 3.96 (s, 3H, 5MeO), 3.97 (s, 3H, 7MeO).

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-1a5052f67ef94db3943b25360ba0cb67
Source dataset
uspto-grants-1997_12
Patent number
US05698575

Reaction notes

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