Methyl iodide → HCID 20346359, compound

HRID 1701706Notes

Reaction equation

HRID 1701706 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:10]2[NH:9][C:8]1=[O:16].[OH-].[Na+].[CH3:19]I>CO>[CH3:19][N:9]1[C:10]2[C:11](=[N:12][CH:13]=[CH:14][CH:15]=2)[N:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[C:8]1=[O:16]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 20346356HCID 20346356, compound

Product 1

HCID 20346359HCID 20346359, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 10.6 g of the product of Step C and 5 g of sodium hydroxide pastilles in 800 ml of methanol was refluxed for 30 minutes and the mixture was then stirred at room temperature until complete dissolution occured (about 2 hours). 45.6 g of methyl iodide were then added dropwise and the mixture was stirred for another 4 hours at room temperature and then allowed to stand overnight. The mixture was evaporated to dryness and the residue was dissolved in 700 ml of water. The aqueous phase was made alkaline with 30% sodium hydroxide solution and was extracted with chloroform. The organic phase was dried over anhydrous sodium sulfate and was filtered and the filtrate was evaporated to dryness. The residue was taken up in petroleum ether and the mixture was filtered. The product was crystallized from an xylene-petroleum ether mixture to obtain 7 g (62% yield) of 1-methyl-3-(2-pyridyl)-1,3-dihydro-imidazo-(4,5-b)-pyridin-2-one in the form of lightly colored pale yellow crystals melting at 128° -130° C.

Workup

  1. temperaturewas refluxed for 30 minutes
  2. custom(about 2 hours)
  3. stirringthe mixture was stirred for another 4 hours at room temperature
  4. customThe mixture was evaporated to dryness
  5. dissolutionthe residue was dissolved in 700 ml of water
  6. extractionwas extracted with chloroform
  7. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  8. filtrationwas filtered
  9. customthe filtrate was evaporated to dryness
  10. filtrationthe mixture was filtered
  11. customThe product was crystallized from an xylene-petroleum ether mixture

Sources & evidence

ORD record
ord-3dbf54cff2ee4551ae070dbb7b6bfb33
Source dataset
uspto-grants-1980_03
Patent number
US04195088

Reaction notes

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