Sodium Thiosulfate → 5-Acetyl-6-methyl-2-[[(3,4-methylenedioxy-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole

HRID 1647153Notes

Reaction equation

HRID 1647153 reaction equation
[C:1]([C:4]1[C:23]([CH3:24])=[CH:22][C:7]2[NH:8][C:9]([S:11][CH2:12][C:13]3[C:18]4[O:19][CH2:20][O:21][C:17]=4[CH:16]=[CH:15][N:14]=3)=[N:10][C:6]=2[CH:5]=1)(=[O:3])[CH3:2].C1C=C(Cl)C=C(C(OO)=[O:33])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl.C(=O)([O-])O.[Na+]>[C:1]([C:4]1[C:23]([CH3:24])=[CH:22][C:7]2[NH:8][C:9]([S:11]([CH2:12][C:13]3[C:18]4[O:19][CH2:20][O:21][C:17]=4[CH:16]=[CH:15][N:14]=3)=[O:33])=[N:10][C:6]=2[CH:5]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 537903565-Acetyl-6-methyl-2-[[(3,4-methylenedioxy-2pyridinyl)methyl]thio]-1H-benzimidazole

Product 1

HCID 539292725-Acetyl-6-methyl-2-[[(3,4-methylenedioxy-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

5-Acetyl-6-methyl-2-[[(3,4-methylenedioxy-2pyridinyl)methyl]thio]-1H-benzimidazole (140 mg, 0,41 mmol) was dissolved in methylene chloride (20 ml) and sodium hydrogen carbonate (5 ml,1M). The mixture was stirred at ambient temperature and MCPBA (100 mg, 0.41 mmol, 70%) dissolved in methylene chloride (10 ml) was added portionwise. After 10 min sodium thiosulphate (100 mg) was added whereupon the phases were separated. The organic phase was dried over sodium sulphate, filtered and concentrated under reduced pressure. The residue was chromatographed on silica (CH2Cl2 /MeOH/NH3, 97.5: 2.5: sat.) Yield: 90 mg (61%) of the title compound. Mp: 178°-180° C. (dec., uncorr.).

Workup

  1. additionwas added portionwise
  2. customwere separated
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was chromatographed on silica (CH2Cl2 /MeOH/NH3, 97.5: 2.5: sat.) Yield: 90 mg (61%) of the title compound

Sources & evidence

ORD record
ord-b7deccffa6a24cc8828d0c3dd0fe80c4
Source dataset
uspto-grants-1995_07
Patent number
US05430042

Reaction notes

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