Ethyl cyanoacetate → HCID 69586072, compound

HRID 2216920Notes

Reaction equation

HRID 2216920 reaction equation
[CH2:1]([C:3]1[C:7]([CH2:8][CH3:9])=[CH:6][NH:5][C:4]=1[CH:10]=O)[CH3:2].[C:12]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])#[N:13].C(NCC)C>C(O)C>[CH2:18]([O:17][C:15](=[O:16])[C:14]([C:12]#[N:13])=[CH:10][C:4]1[NH:5][CH:6]=[C:7]([CH2:8][CH3:9])[C:3]=1[CH2:1][CH3:2])[CH3:19]

Participants

5

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 8021DiethylamineHCID 3593523,4-diethyl-2-formylpyrrole

Product 1

HCID 69586072HCID 69586072, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The 3,4-diethyl-2-formylpyrrole (14.1 g, 93.1 mmol) was dissolved in 200 mL of dry ethanol, and ethyl cyanoacetate (20 mL, 137.9 mmol) and diethylamine (20 mL, 193.3 mmol) were added to the solution. The reaction mixture was heated to reflux under an inert atmosphere and stirred under reflux for 2 hours, after which it was cooled to room temperature and then placed in an ice bath. The resulting dark suspension was filtered through a medium filter, and the light brown solids were washed with cold ethanol. The collected filtrates were concentrated under reduced pressure, precipitating more solids. The thick suspension was filtered, and the combined solids were separated and purified to give 2-cyano-3-(3,4-diethyl -1H-pyrrol-2-yl) acrylic acid ethyl ester, a compound of formula 201 in which R1 and R2 are both ethyl.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux under an inert atmosphere
  3. temperatureunder reflux for 2 hours
  4. customplaced in an ice bath
  5. filtrationThe resulting dark suspension was filtered through a medium
  6. filtrationfilter
  7. washthe light brown solids were washed with cold ethanol
  8. concentrationThe collected filtrates were concentrated under reduced pressure
  9. customprecipitating more solids
  10. filtrationThe thick suspension was filtered
  11. customthe combined solids were separated
  12. custompurified

Sources & evidence

ORD record
ord-e58081ba8490480384163e6cdaf935c1
Source dataset
uspto-grants-2006_09
Patent number
US07112671B2

Reaction notes

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