Ethyl Acetoacetate → HCID 20498940, compound

HRID 2166769Notes

Reaction equation

HRID 2166769 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].Cl.[CH:13]1([CH:18]([NH:20][C:21]2[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=2)[CH3:19])[CH2:17][CH2:16][CH2:15][CH2:14]1>COCCOC>[CH:13]1([CH:18]([NH:20][C:21]2[CH:29]=[CH:28][C:24]([C:25]([CH:2]([C:3]([CH3:5])=[O:4])[C:1]([O:7][CH2:8][CH3:9])=[O:6])=[O:26])=[CH:23][CH:22]=2)[CH3:19])[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 24758Sodium hydrideHCID 20498872HCID 20498872, compound

Product 1

HCID 20498940HCID 20498940, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent3×

Procedure

A solution of 21.6 g. of ethyl acetoacetate and 10 ml. of 1,2-dimethoxyethane is added to a suspension of 4.0 g. of sodium hydride in 1,2-dimethoxyethane under argon. A solution of 17.3 g. of 4-(1-cyclopentylethylamino)benzoyl chloride hydrochloride in 1,2-dimethoxyethane is then added. The reaction mixture is refluxed for 5 hours, cooled, poured on ice and extracted with ether. The ether solution is washed with water and saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated to dryness. Recrystallization from ether affords ethyl 2-[4-(1-cyclopentylethylamino)benzoyl]acetoacetate as a white solid.

Workup

  1. temperatureThe reaction mixture is refluxed for 5 hours
  2. temperaturecooled
  3. additionpoured on ice
  4. extractionextracted with ether
  5. washThe ether solution is washed with water and saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated to dryness
  8. customRecrystallization from ether

Sources & evidence

ORD record
ord-760316c48c7b4e76a0631f1319464e6f
Source dataset
uspto-grants-1983_06
Patent number
US04388459

Reaction notes

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