Sodium Sulfite → HCID 14461510, compound

HRID 1904753Notes

Reaction equation

HRID 1904753 reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[C:6]([CH2:11][S:12][C:13]3[NH:14][C:15]4[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=4[N:17]=3)[N:7]=[CH:8][CH:9]=2)[S:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:30])C=1.S([O-])([O-])=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl.CO>[Br:1][C:2]1[C:10]2[C:5](=[C:6]([CH2:11][S:12]([C:13]3[NH:17][C:16]4[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=4[N:14]=3)=[O:30])[N:7]=[CH:8][CH:9]=2)[S:4][CH:3]=1

Participants

7

Reactant 4

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 20037717HCID 20037717, compound

Product 1

HCID 14461510HCID 14461510, compoundYield 65.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 90 mg (0.239 mmol) of 2-[(3-bromothieno[2,3-c]pyridin-7-yl)methylthio]benzimidazole (Ia-6) in 4 ml of CHCl3 and 1 ml of MeOH was added 52 mg (1.0 equivalent) of 80% m-CPBA at -20° C., and the mixture was stirred for 1 hr. at -20° C. When 10% aqueous sodium sulfite and saturated aqueous NaHCO3 were added to the mixture, crystals separated out and collected by filtration. The extract of the mother liquid with CHCl3 was combined with the crystals and subjected to silica gel column chromatography for purification, whereby 61 mg (Yield : 65.0%) of 2-[(3-bromothieno[2, 3-c]pyridin-7-yl)methylsulfinyl]benzimidazole (Ic-18) was obtained as an objective compound.

Workup

  1. customat -20° C
  2. customseparated out
  3. filtrationcollected by filtration
  4. extractionThe extract of the mother liquid with CHCl3
  5. customsubjected to silica gel column chromatography for purification

Sources & evidence

ORD record
ord-f1f67ccc812e4ace80a3f9565e710409
Source dataset
uspto-grants-1989_06
Patent number
US04839365

Reaction notes

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