Sodium Thiosulfate → 5-acetyl-6-methyl-2-[[(4cyclopropylmethoxy-3-methoxy-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole

HRID 1647155Notes

Reaction equation

HRID 1647155 reaction equation
[C:1]([C:4]1[C:27]([CH3:28])=[CH:26][C:7]2[NH:8][C:9]([S:11][CH2:12][C:13]3[C:18]([O:19][CH3:20])=[C:17]([O:21][CH2:22][CH:23]4[CH2:25][CH2:24]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:37])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl.C(=O)([O-])O.[Na+]>[C:1]([C:4]1[C:27]([CH3:28])=[CH:26][C:7]2[NH:8][C:9]([S:11]([CH2:12][C:13]3[C:18]([O:19][CH3:20])=[C:17]([O:21][CH2:22][CH:23]4[CH2:25][CH2:24]4)[CH:16]=[CH:15][N:14]=3)=[O:37])=[N:10][C:6]=2[CH:5]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 199264465-Acetyl-6-methyl-2-[[(4-cyclopropylmethoxy-3-methoxy-2-pyridinyl)methyl]thio]-1H-benzimidazole

Product 1

HCID 199264755-acetyl-6-methyl-2-[[(4cyclopropylmethoxy-3-methoxy-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

5-Acetyl-6-methyl-2-[[(4-cyclopropylmethoxy-3-methoxy-2-pyridinyl)methyl]thio]-1H-benzimidazole (40 mg, 0.10 mmol) was dissolved in methylene chloride (10 ml) and sodium hydrogen carbonate (3 ml,1M). The mixture was stirred at ambient temperature and MCPBA (25 mg, 0.10 mmol, 70%) dissolved in methylene chloride (5 ml) was added portionwise. After 10 min sodium thiosulphate (30 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 30 mg (73%) of the title compound.

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 30 mg (73%) of the title compound

Sources & evidence

ORD record
ord-54b15deb151640e3abf13f0a09ee5cce
Source dataset
uspto-grants-1995_07
Patent number
US05430042

Reaction notes

Loading…