Iodoethane → HCID 53911617, compound

HRID 1195716Notes

Reaction equation

HRID 1195716 reaction equation
[O-]CC.[Na+].[Na].[Br-].[NH2:7][C:8]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][N+:9]=1[CH2:15][C:16]([O:18][CH2:19][CH3:20])=O.[CH2:21]([O:28][C:29]([C:31]([C:36]#[N:37])=[CH:32]OCC)=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(I)C>C(O)C.CN(C)C=O>[CH2:21]([O:28][C:29]([C:31]([C:36]#[N:37])=[CH:32][C:15]1[N:9]2[CH:10]=[CH:11][CH:12]=[C:13]([CH3:14])[C:8]2=[N:7][C:16]=1[O:18][CH2:19][CH3:20])=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

8

Reactant 5

HCID 6340IodoethaneHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 54512535HCID 54512535, compoundHCID 86745771HCID 86745771, compound

Product 1

HCID 53911617HCID 53911617, compoundYield 43.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred sodium ethoxide solution, freshly prepared with 140 mg of sodium in 30 ml of absolute ethanol, was added 850 mg (3 mmol) of 2-amino-1-(ethoxycarbonylmethyl)-3-methylpyridinium bromide, then the mixture was stirred for 30 min at room temperature. The reaction mixture was treated with 1-(benzyloxycarbonyl)-1-cyano-2-ethoxyethylene (710 mg; 3 mmol) followed by stirred for 30 min at room temperature. The resultant precipitates were collected by filtration, dried, then dissolved in 8 ml of N,N-dimethylformamide (DMF). Ethyl iodide (0.32 ml; 4 mmol) was added to the DMF solution and the mixture was stirred for 2 hours at 60° C. The reaction mixture was cooled at room temperature, extracted with ethyl acetate, the solution was washed with water, dried over anhydrous magnesium sulfate, successively. After removal of the solvent, the residue was chromatographed over silica-gel [eluant: n-hexane-ethyl acetate (1:1)] to give 470 mg (yield: 43%) of the titled compound as yellow needles.

Workup

  1. stirringby stirred for 30 min at room temperature
  2. customThe resultant precipitates
  3. filtrationwere collected by filtration
  4. customdried
  5. dissolutiondissolved in 8 ml of N,N-dimethylformamide (DMF)
  6. stirringthe mixture was stirred for 2 hours at 60° C
  7. temperatureThe reaction mixture was cooled at room temperature
  8. extractionextracted with ethyl acetate
  9. washthe solution was washed with water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customAfter removal of the solvent
  12. customthe residue was chromatographed over silica-gel [eluant: n-hexane-ethyl acetate (1:1)]

Sources & evidence

ORD record
ord-232fbbf36ba648b19bc15595fd7303ef
Source dataset
uspto-grants-1992_05
Patent number
US05112833

Reaction notes

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