Potassium Carbonate → HCID 19973443, compound

HRID 1757115Notes

Reaction equation

HRID 1757115 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]=[C:15]([CH3:17])[N:16]=2)[CH:13]=1.ClC1C=CC=C(C(OO)=[O:26])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+]>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]=[C:15]([CH3:17])[N:16]=2)[CH:13]=1)=[O:26]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 19973464HCID 19973464, compound

Product 1

HCID 19973443HCID 19973443, compoundYield 79.7%

Reagents, catalysts & solvents 2

HCID 70297m-Chloroperbenzoic acidCatalystHCID 6344DichloromethaneSolvent2×

Procedure

4.95 g of the 6-((4-chlorobutyl)thiomethyl)-2-methylimidazo[1,2-a]pyridine prepared in the Preparative Example 17 was dissolved in 50 ml of dichloromethane, followed by the cooling of the obtained solution with ice. A solution of 3.18 g of m-chloroperbenzoic acid in 20 ml of dichloromethane was dropped into the resulting solution in 20 minutes. After one hour, 0.16 g of m-chloroperbenzoic acid was further added to the obtained mixture. The obtained mixture was additionally stirred for 30 minutes, followed by the addition of an aqueous solution of sodium thiosulfate. The obtained mixture was vigorously stirred at room temperature for 15 minutes, followed by the addition of an aqueous solution of potassium carbonate. The obtained mixture was extracted with dichloromethane. The organic phase was dried over anhydrous potassium carbonate and distilled to remove the solvent. The residue was purified by silica gel column chromatography [solvent: dichloromethane/methanol (50:1 to 30:1)] to give 4.18 g of the title compound as a pale-pink solid (yield: 79%).

Workup

  1. temperaturecooling of the obtained solution with ice
  2. stirringThe obtained mixture was vigorously stirred at room temperature for 15 minutes
  3. extractionThe obtained mixture was extracted with dichloromethane
  4. dry with materialThe organic phase was dried over anhydrous potassium carbonate
  5. distillationdistilled
  6. customto remove the solvent
  7. customThe residue was purified by silica gel column chromatography [solvent: dichloromethane/methanol (50:1 to 30:1)]

Sources & evidence

ORD record
ord-94ac2a2e46754336811c31b7305a7735
Source dataset
uspto-grants-1995_08
Patent number
US05444066

Reaction notes

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