Benzimidazole → HCID 21465575, compound

HRID 1939995Notes

Reaction equation

HRID 1939995 reaction equation
Br[C:2]1[C:11](=[S: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](=[S:12])[CH:2]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

5

Reactant 3

HCID 5798BenzimidazoleHCID 11430Potassium CarbonateHCID 57281258HCID 57281258, compound

Product 1

HCID 21465575HCID 21465575, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an eggplant type flask (25 ml), 3-bromothiochromone (121 mg) prepared in Example 8, bezimidazole (236 mg), potassium carbonate (1382 mg), and dimethylformamide (15 ml) were added. The mixture was reacted at 80° C. for 20 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 recrystallized from benzene/hexane to give the titled compound (133 mg; yield=95.3%) as white needle crystals. Melting point: 160°-161° C. 1H-NMR(CDCl3, δ ppm): 7.22 (s, H3), 8.59 (d, H5), 7.64 (t, H6), 7.73 (t, H7), 7.70 (m, H8), 8.25 (s, H2'), 7.78-7.93 (m, H4'), 7.40-7.48 (m, H5'), 7.40-7.48 (m, H6'), 7.78-7.93 (m, H7').

Workup

  1. customThe mixture was reacted at 80° C. for 20 hours
  2. extractionextracted with 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-35b39add1bd9494ba2419532ba1af5f7
Source dataset
uspto-grants-1997_12
Patent number
US05698575

Reaction notes

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