Methyl iodide → HCID 54528366, compound

HRID 1195715Notes

Reaction equation

HRID 1195715 reaction equation
C1CCN2C(=NCCC2)CC1.[Br-].[NH2:13][C:14]1[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][N+:15]=1[CH2:21][C:22]([O:24][CH2:25]C)=O.[C:27]([C:29]([C:34]([O:36][CH2:37][CH3:38])=[O:35])=[CH:30]OCC)#[N:28].CI>ClCCl.CC(C)=O>[C:27]([C:29]([C:34]([O:36][CH2:37][CH3:38])=[O:35])=[CH:30][C:21]1[N:15]2[CH:16]=[CH:17][CH:18]=[C:19]([CH3:20])[C:14]2=[N:13][C:22]=1[O:24][CH3:25])#[N:28]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl esterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86745771HCID 86745771, compound

Product 1

HCID 54528366HCID 54528366, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent2×

Procedure

Eight ml of 1,8-diazabicyclo[5,4,0]-7-undecene was added dropwise to a mixture of 2-amino-1-(ethoxycarbonylmethyl)-3-methylpyridinium bromide (5.5 g; 20 mmol) and dichloromethane (200 ml), and then the mixture was stirred for 30 min at room temperature. To the stirred mixture was dropped 1-cyano-1-(ethoxycarbonyl)-2-ethoxyethylene (3.4 g; 20 mmol) in dichloromethane (100 ml) and the mixture was further stirred for 30 min at room temperature. The mixture was evaporated, and the resultant residue was dissolved in 200 ml of acetone. Methyl iodide (20 ml; 32 mmol) was added to the acetone solution and the solution was heated under reflux for 1.5 hour at 60° C. After standing for several hours at room temperature, the resultant precipitates were removed by filtration. The filtrate was concentrated, and the residue was dissolved in dichloromethane, the solution was washed with water, dried over anhydrous magnesium sulfate, successively. The residue, obtained by evaporating the solvent, was chromatographed over silicagel [eluant: hexane-ethyl acetate (2:1)] to give 3.12 g (yield: 55%) of the titled compound as yellow needles.

Workup

  1. stirringthe mixture was further stirred for 30 min at room temperature
  2. customThe mixture was evaporated
  3. dissolutionthe resultant residue was dissolved in 200 ml of acetone
  4. temperaturethe solution was heated
  5. temperatureunder reflux for 1.5 hour at 60° C
  6. waitAfter standing for several hours at room temperature
  7. customthe resultant precipitates
  8. customwere removed by filtration
  9. concentrationThe filtrate was concentrated
  10. dissolutionthe residue was dissolved in dichloromethane
  11. washthe solution was washed with water
  12. dry with materialdried over anhydrous magnesium sulfate
  13. customThe residue, obtained
  14. customby evaporating the solvent
  15. customwas chromatographed over silicagel [eluant: hexane-ethyl acetate (2:1)]

Sources & evidence

ORD record
ord-4545f58377ed46a382d97e672d12b245
Source dataset
uspto-grants-1992_05
Patent number
US05112833

Reaction notes

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