Sodium Sulfite → HCID 14461506, compound

HRID 1904750Notes

Reaction equation

HRID 1904750 reaction equation
[CH2:1]([O:3][C:4]([O:6][CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[S:17][CH2:18][C:19]1[N:20]=[CH:21][CH:22]=[C:23]2[CH:27]=[CH:26][S:25][C:24]=12)=[O:5])[CH3:2].C1C=C(Cl)C=C(C(OO)=[O:36])C=1.C([O-])(O)=O.[Na+].S([O-])([O-])=O.[Na+].[Na+]>CCOCC.O>[CH2:1]([O:3][C:4]([O:6][CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[S:17]([CH2:18][C:19]1[N:20]=[CH:21][CH:22]=[C:23]2[CH:27]=[CH:26][S:25][C:24]=12)=[O:36])=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 14461495HCID 14461495, compound

Product 1

HCID 14461506HCID 14461506, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 279.6 mg (0.700 mmol) of 1-ethoxycarbonyloxymethyl-2-[(thieno[2, 3-c]pyridin-7-yl)methylthio]benzimidazole (Ib-11) in 30 ml of CHCl, was mixed with 226.5 mg (1.05 mmol) of 80% m-CPBA at -10° to -15° C., and stirred for 1 hr. The mixture was treated with 3 ml of saturated aqueous NaHCO3 and 0.6 ml of 10% aqueous sodium sulfite, and after bringing back to room temperature, the solution was mixed with water and extracted with CHCl3. After drying CHCl3 layer over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure, whereby brown viscous liquid was obtained. After silica gel column chromatography, the crystals were dispersed with 3 ml of ether, followed by filtration and washed with ether, whereby 158.0 mg (Yield : 54.3%) of the objective compound (Ic-17), 1-ethoxycarbonyloxymethyl-2-[(thieno[2, 3-c]pyridin-7-yl]methylsulfinyl]benzimidazole was obtained as crystals.

Workup

  1. customafter bringing back to room temperature
  2. extractionextracted with CHCl3
  3. dry with materialAfter drying CHCl3 layer over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure, whereby brown viscous liquid
  5. customwas obtained
  6. filtrationfollowed by filtration
  7. washwashed with ether, whereby 158.0 mg (Yield : 54.3%) of the objective compound (Ic-17)

Sources & evidence

ORD record
ord-7ef3a315a623496eaed9c471bab3bd83
Source dataset
uspto-grants-1989_06
Patent number
US04839365

Reaction notes

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