Sodium Sulfite → HCID 14461509, compound

HRID 1904751Notes

Reaction equation

HRID 1904751 reaction equation
[S:1]1[C:9]2[CH:8]=[CH:7][N:6]=[C:5]([CH2:10][S:11][C:12]3[NH:13][C:14]4[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=4[N:16]=3)[C:4]=2[CH:3]=[CH:2]1.C1C=C(Cl)C=C(C(OO)=[O:29])C=1.C([O-])(O)=O.[Na+].S([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl.O.CO>[S:1]1[C:9]2[CH:8]=[CH:7][N:6]=[C:5]([CH2:10][S:11]([C:12]3[NH:13][C:14]4[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=4[N:16]=3)=[O:29])[C:4]=2[CH:3]=[CH:2]1

Participants

8

Reactant 4

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 14461508HCID 14461508, compound

Product 1

HCID 14461509HCID 14461509, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 6212ChloroformSolvent

Procedure

To a solution of 278.6 mg (0.900 mmol) of 2-[(thieno[3, 2-c]pyridin-4-yl)methylthio]benzimidazole.2/3 H2O (Ia') in 20 ml of CHCl3 and 1 ml of MeOH was added 194.1 mg (0.900 mmol) of 80% mCPBA at -10° to -15° C. and stirred for 30 minutes. To the mixture were added 2.5 ml of saturated aqueous NaHCO3 and 0.5 ml of 10 % aqueous sodium sulfite. After bringing back to room temperature, water was added thereto, and the solution was extracted with CHCl3. After drying CHCl3 layer over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure and washed with ether, whereby 274.6 mg (Yield : 92.5%) of the objective compound (Ic'), 2-[(thieno[3, 2-c]pyridin-4-yl)methylsulfinyl]benzimidazole was obtained as crystals.

Workup

  1. customAfter bringing back to room temperature
  2. extractionthe solution was extracted with CHCl3
  3. dry with materialAfter drying CHCl3 layer over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. washwashed with ether, whereby 274.6 mg (Yield : 92.5%) of the objective compound (Ic'), 2-[(thieno[3, 2-c]pyridin-4-yl)methylsulfinyl]benzimidazole
  6. customwas obtained as crystals

Sources & evidence

ORD record
ord-cbc54643b993497abd88b3a177e80e02
Source dataset
uspto-grants-1989_06
Patent number
US04839365

Reaction notes

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