Benzimidazole → HCID 13738537, compound

HRID 1939989Notes

Reaction equation

HRID 1939989 reaction equation
I[C:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[O:4][CH:3]=1.[N:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[NH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[NH:15][C:14]=1[C:3]1[O:4][C:5]2[C:10]([C:11](=[O:12])[CH:2]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

5

Reactant 3

HCID 5798BenzimidazoleHCID 11430Potassium CarbonateHCID 109017203-Iodo-4H-chromen-4-one

Product 1

HCID 13738537HCID 13738537, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an eggplant type flask (25 ml), 3-iodochromone (136 mg) prepared in Example 1, benzimidazole (236 mg), potassium carbonate (1382 mg), and dimethylformamide (15 ml) were added and the mixture was reacted at 80° C. for 2 hours with stirring. The reaction mixture was added to ice water and extracted with 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 the purified compound was recrystallized from benzene/hexane to give the titled compound (114.5 mg; yield=87.0 %) as white needle crystals. Melting point: 232° C. 1H-NMR(CDCl3, δ ppm): 6.59 (s, H3), 8.28 (dd, H5), 7.48-7.64 (m, H6), 7.78 (t, H7), 7.48-7.64 (m, H8), 8.48 (s, H2'), 7.86-7.94 (m, H4'), 7.45-7.50 (m, H5'), 7.45-7.50 (m, H6'), 7.86-7.94 (m, H7').

Workup

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

Sources & evidence

ORD record
ord-1be974d2f35f4dd3a8271595c0014913
Source dataset
uspto-grants-1997_12
Patent number
US05698575

Reaction notes

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