m-Chloroperbenzoic acid → 2-[(3,4-Dimethoxypyrid-2-yl)methylsulfinyl]benzimidazole

HRID 649219Notes

Reaction equation

HRID 649219 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH2:11][S:12][C:13]2[NH:14][C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[N:17]=2)=[N:5][CH:6]=[CH:7][C:8]=1[O:9][CH3:10].ClC1C=CC=C(C(OO)=[O:30])C=1>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:4]([CH2:11][S:12]([C:13]2[NH:17][C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=3[N:14]=2)=[O:30])=[N:5][CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 139829512-[(3,4-Dimethoxypyrid-2-yl)methylthio]benzimidazole

Product 1

HCID 139829522-[(3,4-Dimethoxypyrid-2-yl)methylsulfinyl]benzimidazoleYield 58.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-[(3,4-dimethoxypyrid-2-yl)methylthio]benzimidazole (1.08 g) in methylene chloride (30 ml) was added m-chloroperbenzoic acid (0.79 g) in small protions below 10° C. After completion of the reaction the reaction, the mixture was diluted with methylene chloride (70 ml), washed with an aqueous solution of potassium carbonate and then with water, dried, and evaporated. The residue was purified by column chromatography on silica gel (chloroform-methanol (40:1)) and crystallized from acetone-ether, to give 2-[(3,4-dimethoxypyrid-2-yl)methylsulfinyl]benzimidazole (670 mg) as light brown crystals. m.p. 149°-151° C. (decomposed).

Workup

  1. customAfter completion of the reaction
  2. customthe reaction
  3. washwashed with an aqueous solution of potassium carbonate
  4. dry with materialwith water, dried
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica gel (chloroform-methanol (40:1))
  7. customcrystallized from acetone-ether

Sources & evidence

ORD record
ord-d183f4e9f7cf419ba23eb8b21fbf89de
Source dataset
uspto-grants-1988_04
Patent number
US04738975

Reaction notes

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