Sodium Thiosulfate → HCID 19973458, compound

HRID 1440237Notes

Reaction equation

HRID 1440237 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][S:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]2[N:12]([CH:14]=[CH:15][N:16]=2)[CH:13]=1.ClC1C=CC=C(C(OO)=[O:25])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl.ClC1C=CC=C(C(OO)=O)C=1>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][S:6]([CH2:7][C:8]1[CH:9]=[CH:10][C:11]2[N:12]([CH:14]=[CH:15][N:16]=2)[CH:13]=1)=[O:25]

Participants

6

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 19973453HCID 19973453, compound

Product 1

HCID 19973458HCID 19973458, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 70297m-Chloroperbenzoic acidCatalystHCID 6344DichloromethaneSolvent

Procedure

11.79 g of the 6-((4-chlorobutyl)thiomethyl)imidazo[1,2-a]pyridine prepared in the Preparative Example 7 was dissolved in 160 ml of dichloromethane. The obtained solution was cooled with ice, followed by the addition of 7.99 g of m-chloroperbenzoic acid in about 40 minutes. The obtained mixture was stirred. After 30 minutes, 0.4 g of m-chloroperbenzoic acid was further added thereto. The obtained mixture was additionally stirred for one hour, followed by the addition of an aqueous solution of sodium thiosulfate. The obtained mixture was vigorously stirred at room temperature for 30 minutes and extracted with chloroform. The organic phase was washed with an aqueous solution of potassium carbonate, dried over anhydrous magnesium sulfate, and distilled to remove the solvent. The obtained residue was purified by silica gel column chromatography [solvent: dichloromethane/methanol (80:1 to 10:1)] to give 9.51 g of the title compound as a dark-creamy oil (yield: 76%).

Workup

  1. temperatureThe obtained solution was cooled with ice
  2. stirringThe obtained mixture was additionally stirred for one hour
  3. stirringThe obtained mixture was vigorously stirred at room temperature for 30 minutes
  4. extractionextracted with chloroform
  5. washThe organic phase was washed with an aqueous solution of potassium carbonate
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationdistilled
  8. customto remove the solvent
  9. customThe obtained residue was purified by silica gel column chromatography [solvent: dichloromethane/methanol (80:1 to 10:1)]

Sources & evidence

ORD record
ord-a648b72bf5954729b66c9490b40e93b5
Source dataset
uspto-grants-1996_03
Patent number
US05498634

Reaction notes

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