Ethyl cyanoacetate → HCID 86752466, compound

HRID 1599998Notes

Reaction equation

HRID 1599998 reaction equation
[Cl:1][CH2:2][C:3](=[N:7][C:8]#[N:9])OCC.[C:10]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])#[N:11].[O-:18]CC.[Na+]>C(O)C>[Cl:1][CH2:2]/[C:3](/[NH:7][C:8]([NH2:9])=[O:18])=[C:12](\[C:10]#[N:11])/[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

5

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 2723922Sodium ethoxideHCID 2169930890773-43-6

Product 1

HCID 86752466HCID 86752466, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 20 g of ethyl 2-chloro-N-cyanoacetoimidate (20), 16.6 g of ethyl cyanoacetate (21) and 9.28 g of sodium ethoxide in ethanol (350 ml) was stirred at room temperature for 3 hours. After the reaction mixture was distilled, 140 ml of 2N hydrochloric acid were added, followed by stirring under ice cooling for 1 hour. After the reaction mixture was neutralized with a 2N aqueous solution of sodium hydroxide, the resultant mixture was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, and then concentrated underreduced pressure. The residue so obtained was purified by chromatography ona silica gel column while using gradient elution with hexane-ethyl acetate,whereby 5.66 g of the title compound were obtained (yield: 18%).

Workup

  1. distillationAfter the reaction mixture was distilled
  2. addition140 ml of 2N hydrochloric acid were added
  3. extractionthe resultant mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated underreduced pressure
  7. customThe residue so obtained
  8. customwas purified by chromatography ona silica gel column
  9. washelution with hexane-ethyl acetate,whereby 5.66 g of the title compound
  10. customwere obtained (yield: 18%)

Sources & evidence

ORD record
ord-0ee715c4ba4842249ba4bce6c4ef61b6
Source dataset
uspto-grants-1998_04
Patent number
US05744475

Reaction notes

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