Methyl iodide → HCID 20346355, compound

HRID 1701703Notes

Reaction equation

HRID 1701703 reaction equation
[OH-].[Na+].[N:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]3=[N:14][CH:15]=[CH:16][CH:17]=[C:12]3[NH:11][C:10]2=[O:18])=[CH:5][CH:4]=1.[CH3:19]I>CO>[CH3:19][N:11]1[C:12]2[C:13](=[N:14][CH:15]=[CH:16][CH:17]=2)[N:9]([C:6]2[CH:5]=[CH:4][N:3]=[CH:8][CH:7]=2)[C:10]1=[O:18]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 20346361HCID 20346361, compound

Product 1

HCID 20346355HCID 20346355, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5.7 g of sodium hydroxide pastilles were added to a suspension of 15 g of the product of Step B in 700 ml of methanol and complete dissolution occured after a few minutes. The mixture was stirred at room temperature for an hour and after the addition of 45.6 g of methyl iodide thereto, the mixture was stirred at room temperature for another 6 hours. The mixture stood overnight and was then filtered to remove hydroiodide of product melting at 275°-285° C. The filtrate was evaporated to dryness and the combined residue and hydroiodide were dissolved in water. The solution was made alkaline by addition of 30% sodium hydroxide solution and was then extracted with chloroform. The organic phase was dried over anhydrous sodium sulfate and was filtered. The filtrate was evaporated to dryness and the residue was crystallized from 95% ethanol to obtain 4 g (25% yield) of 1-methyl-3-(4-pyridyl)-1,3-dihydro-imidazo-(4,5-b)-pyridin-2-one in the form of a pale crystalline powder melting at 211°-213° C.

Workup

  1. waitoccured after a few minutes
  2. stirringthe mixture was stirred at room temperature for another 6 hours
  3. filtrationwas then filtered
  4. customto remove hydroiodide of product melting at 275°-285° C
  5. customThe filtrate was evaporated to dryness
  6. dissolutionthe combined residue and hydroiodide were dissolved in water
  7. additionby addition of 30% sodium hydroxide solution
  8. extractionwas then extracted with chloroform
  9. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  10. filtrationwas filtered
  11. customThe filtrate was evaporated to dryness
  12. customthe residue was crystallized from 95% ethanol

Sources & evidence

ORD record
ord-5e3414a9ed984a2bb10b1b61a972ccc5
Source dataset
uspto-grants-1980_03
Patent number
US04195088

Reaction notes

Loading…