Sodium Carbonate → 5-Benzoyl-2-(2-pyridylsulfinylmethyl)benzimidazole

HRID 414190Notes

Reaction equation

HRID 414190 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[C:12]([C:20]1[CH:36]=[CH:35][C:23]2[N:24]=[C:25]([CH2:27][S:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=3)[NH:26][C:22]=2[CH:21]=1)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[C:12]([C:20]1[CH:36]=[CH:35][C:23]2[N:24]=[C:25]([CH2:27][S:28]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=3)=[O:6])[NH:26][C:22]=2[CH:21]=1)(=[O:19])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 139611675-Benzoyl-2-(2-pyridylthiomethyl)benzimidazole

Product 1

HCID 139611705-Benzoyl-2-(2-pyridylsulfinylmethyl)benzimidazoleYield 66.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10.1 g (0.05 mole) of 85% pure m-chloroperoxybenzoic acid are added slowly to a solution, cooled to -15° C., of 17.3 g (0.05 mole) of 5-benzoyl-2-(2-pyridylthiomethyl)benzimidazole in 250 ml of dichloromethane. The mixture is stirred at a temperature below -10° C. for 30 minutes and 100 ml of sodium carbonate solution are added. The organic phase is decanted, washed with sodium carbonate and water and then dried (Na2SO4). When this has been filtered, the solvent is evaporated off and the residue recrystallized in acetone. 12.0 g (66.5%) of 5-benzoyl-2-(2-pyridylsulfinylmethyl)benzimidazole, melting point 142°-145° C., are obtained.

Workup

  1. customThe organic phase is decanted
  2. washwashed with sodium carbonate and water
  3. dry with materialdried (Na2SO4)
  4. filtrationWhen this has been filtered
  5. customthe solvent is evaporated off
  6. customthe residue recrystallized in acetone

Sources & evidence

ORD record
ord-1e00a93faf7d423bb98d89f236396c8d
Source dataset
uspto-grants-1988_12
Patent number
US04791114

Reaction notes

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