Sodium Thiosulfate → HCID 54197406, compound

HRID 861327Notes

Reaction equation

HRID 861327 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]([C:11]([C:13]2[CH:18]=[CH:17][C:16]3[O:19][CH2:20][O:21][C:15]=3[CH:14]=2)=[O:12])=[CH:9][CH:8]=[C:7]([CH3:22])[N:6]=1)=[O:4].C1C=C(Cl)C=C(C(OO)=[O:31])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+].C([O-])(O)=O.[Na+]>ClCCl>[CH3:22][C:7]1[N+:6]([O-:31])=[C:5]([C:3]([O:2][CH3:1])=[O:4])[C:10]([C:11]([C:13]2[CH:18]=[CH:17][C:16]3[O:19][CH2:20][O:21][C:15]=3[CH:14]=2)=[O:12])=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 19702868HCID 19702868, compound

Product 1

HCID 54197406HCID 54197406, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a dichloromethane(20 ml) solution of 6-methyl-3-(3,4-methylenedioxyphenylcarbonyl)pyridine-2-carboxylic acid methyl ester(1.75 g,5.85 mmol) was added mCPBA(1.73 g) under ice-cooling. The mixture was stirred at room temperature for 20 h and an aqueous solution of sodium thiosulfate was added to the mixture to quench the reaction. The mixture was neutralized with a saturated aqueous solution of NaHCO3 and extracted with dichloromethane. The organic layer was washed with brine, dried over MgSO4 and concentrated under reduce pressure to give 6-methyl-3-(3,4-methylenedioxyphenylcarbonyl)-2-methoxycarbonylpyridine N-oxide(1.57 g).

Workup

  1. temperaturecooling
  2. customto quench
  3. customthe reaction
  4. extractionextracted with dichloromethane
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-df70440061f94dfeb17cd3a6afb40470
Source dataset
uspto-grants-1998_02
Patent number
US05714479

Reaction notes

Loading…