Sodium Carbonate → HCID 19770953, compound

HRID 1589842Notes

Reaction equation

HRID 1589842 reaction equation
[C:1]([O-])([O-])=O.[Na+].[Na+].[I-].[NH2:8][N+:9]1C=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][CH3:16].[C:17]([O:21][CH2:22][CH3:23])(=[O:20])[C:18]#[CH:19]>CN(C=O)C>[CH2:15]([C:10]1[N:9]2[N:8]=[CH:1][C:18]([C:17]([O:21][CH2:22][CH3:23])=[O:20])=[C:19]2[CH:13]=[CH:12][CH:11]=1)[CH3:16]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 12182Ethyl propiolateHCID 152018911-Amino-2-ethylpyridin-1-ium iodide

Product 1

HCID 19770953HCID 19770953, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Next, 2.2 g (20.8 mmol) of Na2CO3 were added to a solution of 4.5 g (18.0 mmol) of 1-amino-2-ethylpyridinium iodide in 20 ml of DMF, followed by stirring at room temperature for 1 hour. Ethyl propiolate (3.6 g; 36.7 mmol) was added further, followed by stirring at room temperature for 20 hours. The solvent of the reaction mixture was distilled off. Water was added to the residue, followed by extraction with methylene chloride. After the methylene chloride layer was dried over Na2SO4, the solvent was distilled off and the residue was purified by chromatography on a silica gel column, whereby 0.93 g (4.3 mmol) of the title compound was obtained as crystals (yield: 24%-12% in two steps).

Workup

  1. stirringby stirring at room temperature for 20 hours
  2. distillationThe solvent of the reaction mixture was distilled off
  3. additionWater was added to the residue
  4. extractionfollowed by extraction with methylene chloride
  5. dry with materialAfter the methylene chloride layer was dried over Na2SO4
  6. distillationthe solvent was distilled off
  7. customthe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-a63bddb50345421b9532ee0b0f44ac78
Source dataset
uspto-grants-1993_04
Patent number
US05200415

Reaction notes

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