Ethyl cyanoacetate → HCID 86752466, compound

HRID 1274888Notes

Reaction equation

HRID 1274888 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 2 N hydrochloric acid were added, followed by stirring under ice cooling for 1 hour. After the reaction mixture was neutralized with a 2 N 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 under reduced pressure. The residue so obtained was purified by chromatography on a 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 2 N 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 under reduced pressure
  7. customThe residue so obtained
  8. customwas purified by chromatography on a silica gel column
  9. washelution with hexane-ethyl acetate

Sources & evidence

ORD record
ord-57cb0a91b130458b8358eb1df33450e8
Source dataset
uspto-grants-2000_12
Patent number
US06159969

Reaction notes

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