m-Chloroperbenzoic acid → 5,6-Dimethoxy-2-[5-methoxy-2-(2-pyridinyl)phenyl sulphinyl]-1H-benzimidazole

HRID 1199463Notes

Reaction equation

HRID 1199463 reaction equation
[CH3:1][O:2][C:3]1[C:26]([O:27][CH3:28])=[CH:25][C:6]2[NH:7][C:8]([S:10][C:11]3[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:12]=3[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)=[N:9][C:5]=2[CH:4]=1.ClC1C=CC=C(C(OO)=[O:37])C=1>C(OCC)(=O)C>[CH3:1][O:2][C:3]1[C:26]([O:27][CH3:28])=[CH:25][C:6]2[NH:7][C:8]([S:10]([C:11]3[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:12]=3[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)=[O:37])=[N:9][C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 198666535,6-Dimethoxy-2-[5-methoxy-2-(2-pyridinyl)phenylthio]-1H-benzimidazole

Product 1

HCID 150595155,6-Dimethoxy-2-[5-methoxy-2-(2-pyridinyl)phenyl sulphinyl]-1H-benzimidazole

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

The product of step (c) above (370 mg) was dissolved in ethyl acetate (90 ml) and cooled to -10°. To the stirred solution was added a solution of m-chloroperbenzoic acid (191 mg of 85%) in ethyl acetate (10 ml). After stirring for 1 hour the solution was washed with sodium bicarbonate solution, sodium metabisulphite solution, water and brine then dried and evaporated. The residue was flash chromatographed to afford the title compound as a buff solid, mp 208°-210°.

Workup

  1. temperaturecooled to -10°
  2. washwas washed with sodium bicarbonate solution, sodium metabisulphite solution, water and brine
  3. customthen dried
  4. customevaporated
  5. customchromatographed

Sources & evidence

ORD record
ord-07b88f599cdd4f95bdbf3cf965fe4999
Source dataset
uspto-grants-1990_02
Patent number
US04900751

Reaction notes

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