Methanesulfonic Acid → HCID 15045507, compound

HRID 1030514Notes

Reaction equation

HRID 1030514 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]([CH2:12][S:13][C:14]2[S:15][C:16]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)=[N:17][N:18]=2)=[N:10][CH:11]=1)=[O:5])[CH3:2].CS(O)(=O)=[O:27].OOS([O-])=O.[K+].C(=O)([O-])O.[Na+]>O.C(O)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]([CH2:12][S:13]([C:14]2[S:15][C:16]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)=[N:17][N:18]=2)=[O:27])=[N:10][CH:11]=1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 6395Methanesulfonic AcidHCID 516892Sodium BicarbonateHCID 15045506HCID 15045506, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 15045507HCID 15045507, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixed solution of 4.92 g of 2-[(5-ethoxycarbonylpyridin-2-yl)methylthio]-5-(3-pyridyl)-1,3,4-thiadiazole, 2.7 ml of methane-sulfonic acid, 18 ml of acetic acid, and 45 ml of water was cooled to 0° C., oxone (4.65 g) was added to the solution, and the mixture was stirred for 3 hours. The reaction mixture was neutralized with an aqueous solution of sodium hydrogencarbonate so that the pH value was 5, and the mixture was extracted with dichloromethane. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, the residue was separated and purified by silica gel column chromatography (chloroform/methanol=30/1), and a fraction having an Rf value of 0.25 was recrystallized from ethanol to obtain 2.45 g of 2-[(5-ethoxycarbonylpyridin-2-yl)methylsulfinyl]-5-(3-pyridyl)-1,3,4-thiadiazole.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was separated
  6. custompurified by silica gel column chromatography (chloroform/methanol=30/1)
  7. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-9833b1a7f7b34506938954acb75f9f30
Source dataset
uspto-grants-1992_04
Patent number
US05106859

Reaction notes

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