Sodium Sulfite → HCID 14461501, compound

HRID 1904749Notes

Reaction equation

HRID 1904749 reaction equation
[C:1]([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])[CH2:2][CH2:3][CH3:4].C1C=C(Cl)C=C(C(OO)=[O:36])C=1.C([O-])(O)=O.[Na+].S([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl.CCOCC.O>[C:1]([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])[CH2:2][CH2:3][CH3:4]

Participants

8

Reactant 4

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 14461490HCID 14461490, compound

Product 1

HCID 14461501HCID 14461501, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 318.0 mg (0.800 mmol) of 1-butyryloxymethyl-2-[(thieno[2, 3-c]pyridin-7-yl)methylthio]benzimidazole (Ib-6) in 30 ml of CHCl3 was added 224.3 mg (1.04 mmol) of 80% m-CPBA at -10° to -15 ° C., and the mixture was stirred for 1 hr. To the solution were added 3 ml of saturated aqueous NaHCO3 and 0.6 ml of 10% aqueous sodium sulfite. 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 ether, followed by filtration and washed with ether, whereby 169.8 mg (Yield : 51.3%) of the objective compound (Ic-12), 1-butyryloxymethyl-2-[(thieno[2, 3-c]pyridin7-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 169.8 mg (Yield : 51.3%) of the objective compound (Ic-12)

Sources & evidence

ORD record
ord-2e3ceec6cd2c403ab05e922424629c4d
Source dataset
uspto-grants-1989_06
Patent number
US04839365

Reaction notes

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