Sodium Sulfite → HCID 14461511, compound

HRID 1904755Notes

Reaction equation

HRID 1904755 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[C:9]([CH2:14][S:15][C:16]3[NH:17][C:18]4[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=4[N:20]=3)[N:10]=[CH:11][CH:12]=2)[S:7][CH:6]=1)=[O:4].C1C=C(Cl)C=C(C(OO)=[O:33])C=1.S([O-])([O-])=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl.CO>[C:3]([C:5]1[C:13]2[C:8](=[C:9]([CH2:14][S:15]([C:16]3[NH:17][C:18]4[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=4[N:20]=3)=[O:33])[N:10]=[CH:11][CH:12]=2)[S:7][CH:6]=1)([O:2][CH3:1])=[O:4]

Participants

7

Reactant 4

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 53837479HCID 53837479, compound

Product 1

HCID 14461511HCID 14461511, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 140 mg (0.433 mmol) of 2-[(3-methoxycarbonylthieno[2, 3-c]pyridin-7-yl)methylthio]benzimidazole (Ia-10) in 6 ml of CHCl3 and 2 ml of MeOH was added 94 mg (1.1 equivalents) of 80% m-CPBA in the ice-water bath of -10° C., and the mixture was allowed to react for 1 hr. at -10° C. The solution was treated with 10 % aqueous sodium sulfite and saturated aqueous NaHCO3 and extracted with CH2Cl2. The extract was subjected to silica gel column chromatography, eluting with CH2Cl2 --MeOH, and the eluate gave 122 mg (Yield : 75.8%) of 2-[(3-carbomethoxythieno[2, 3-c]pyridin-7-yl)methylsulfinylbenzimidazole (Ic-22) as a foamy product.

Workup

  1. customto react for 1 hr
  2. customat -10° C
  3. extractionextracted with CH2Cl2
  4. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-0379fc589ccc4bf290801a356b4dd38e
Source dataset
uspto-grants-1989_06
Patent number
US04839365

Reaction notes

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