m-Chloroperbenzoic acid → HCID 14622498, compound

HRID 1639010Notes

Reaction equation

HRID 1639010 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C:9]([CH2:15][S:16][C:17]1[NH:18][C:19]3[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=3[N:21]=1)=[N:8][CH:7]=[CH:6]2.C1C=C(Cl)C=C(C(OO)=[O:34])C=1.C([O-])(O)=O.[Na+].OS([O-])=O.[Na+]>C(Cl)(Cl)Cl.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C:9]([CH2:15][S:16]([C:17]1[NH:21][C:20]3[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=3[N:18]=1)=[O:34])=[N:8][CH:7]=[CH:6]2

Participants

7

Reactant 4

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 146224721-{[(1H-Benzimidazol-2-yl)sulfanyl]methyl}-6,7-dimethoxyisoquinolineHCID 23665763Sodium Bisulfite

Product 1

HCID 14622498HCID 14622498, compoundYield 83.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 246.0 mg of 2-[(6,7-dimethoxyisoquinolin-1-yl)methylthio]benzimidazole (Ia-1) (0.700 mmol) in 10 ml of CHCl3 was added 151.0 mg of 80% 3-CPBA (0.700 mmol) at -10°--15° C., and the mixture was stirred for 30 min. at the same temperature. The reaction mixture was mixed with 3 ml of saturated aqueous solution of NaHCO3 and 0.3 ml of 10% aqueous solution of NaHSO3. The reaction temperature was returned to room temperature, and the reaction mixture was mixed with 2 ml of water and extracted with CHCl3. The CHCl3 layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was subjected to silica gel chromatography, eluting with AcOEt-MeOH. The obtained crystals were washed with CH2Cl2 -benzene to give 216.2 mg of the objective compound 2-[(6,7-dimethoxyisoquinolin-1-yl)methylsulfinyl]benzimidazole (Ic-1) (Yield: 83.7%).

Workup

  1. customwas returned to room temperature
  2. extractionextracted with CHCl3
  3. dry with materialThe CHCl3 layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. washeluting with AcOEt-MeOH
  6. washThe obtained crystals were washed with CH2Cl2 -benzene

Sources & evidence

ORD record
ord-e55e0b83cd7149ec90b1859532962332
Source dataset
uspto-grants-1989_11
Patent number
US04882338

Reaction notes

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