Benzimidazole → HCID 12056927, compound

HRID 985445Notes

Reaction equation

HRID 985445 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][CH:2]=1.[H-].[Na+].Cl[C:13]1[N:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][N:14]=1>CN(C)C=O>[CH3:20][O:19][C:17]1[CH:16]=[CH:15][N:14]=[C:13]([N:1]2[C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=[CH:2]2)[N:18]=1

Participants

5

Reactant 3

HCID 5798BenzimidazoleHCID 24758Sodium hydrideHCID 5889352-Chloro-4-methoxypyrimidine

Product 1

HCID 12056927HCID 12056927, compoundYield 41.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Benzimidazole (0.50 g) was dissolved in dimethylformamide (10 ml), and sodium hydride (60% purity, oily) (0.18 g) was added thereto at room temperature. After stirring for 1 hour, 2-chloro-4-methoxypyrimidine (0.62 g) was added at room temperature, followed by stirring for 3 hours. Ice water was added, followed by extraction with ethyl acetate, washing with a saturated sodium chloride aqueous solution and drying over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography to obtain 0.40 g of the desired product as a white powder (m.p. 114-116° C.).

Workup

  1. customat room temperature
  2. stirringby stirring for 3 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. washwashing with a saturated sodium chloride aqueous solution
  5. dry with materialdrying over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b5181a64c6914d9c90fca422bd3d0921
Source dataset
uspto-grants-2005_03
Patent number
US06872729B2

Reaction notes

Loading…