Sodium methanethiolate → 5-Methylthioimidazo[1,2-a]pyridine

HRID 2232431Notes

Reaction equation

HRID 2232431 reaction equation
Cl[C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.[CH3:11][S-:12].[Na+]>CN(C)C=O>[CH3:11][S:12][C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 109537225-Chloroimidazo[1,2-A]pyridine

Product 1

HCID 151443105-Methylthioimidazo[1,2-a]pyridineYield 55.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

Into 100 ml of dimethylformamide are suspended 5 g of 5-chloroimidazo[1,2-a]pyridine and 5 g of sodium methanethiolate and the mixture is stirred at 20° C. for 1 hour. The solvent is evaporated off under reduced pressure and the residue is dissolved in 200 ml of dichloromethane. The mixture is washed with aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate and purified by silica-gel column chromatography to give 3 g of the above-identified compound as an oil.

Workup

  1. customThe solvent is evaporated off under reduced pressure
  2. dissolutionthe residue is dissolved in 200 ml of dichloromethane
  3. washThe mixture is washed with aqueous saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. custompurified by silica-gel column chromatography

Sources & evidence

ORD record
ord-a4648e05eaa5458e8da931f93881c3d6
Source dataset
uspto-grants-1988_11
Patent number
US04788185

Reaction notes

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