Diethyl Malonate → Diethyl 2-(1-tetradec-4-enylamino)benzoylmalonate

HRID 325551Notes

Reaction equation

HRID 325551 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].Cl.[CH2:15]([NH:29][C:30]1[CH:38]=[CH:37][CH:36]=[CH:35][C:31]=1[C:32](Cl)=[O:33])[CH2:16][CH2:17][CH:18]=[CH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>COCCOC>[CH2:15]([NH:29][C:30]1[CH:38]=[CH:37][CH:36]=[CH:35][C:31]=1[C:32]([CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8])=[O:33])[CH2:16][CH2:17][CH:18]=[CH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 737080852-(4-Tetradecenylamino)benzoyl chloride hydrochloride

Product 1

HCID 54437661Diethyl 2-(1-tetradec-4-enylamino)benzoylmalonate

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent3×

Procedure

A solution of 26.6 g. of diethyl malonate 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 2-(1-tetradec-4-enylamino)benzoyl chloride hydrochloride in 1,2-dimethoxyethane is then added. The reaction mixture is refluxed for 4.5 hours, cooled, poured on ice, acidified, 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. Addition of a small amount of ethanol to the residue gives a solid which is filtered and discarded. The ethanol filtrate is concentrated and the residue is recrystallized from ether to yield diethyl 2-(1-tetradec-4-enylamino)benzoylmalonate.

Workup

  1. temperatureThe reaction mixture is refluxed for 4.5 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. additionAddition of a small amount of ethanol to the residue
  9. customgives a solid which
  10. filtrationis filtered
  11. concentrationThe ethanol filtrate is concentrated
  12. customthe residue is recrystallized from ether

Sources & evidence

ORD record
ord-a65a400e7b5a4793b6cf44c5feaf9c19
Source dataset
uspto-grants-1984_04
Patent number
US04440940

Reaction notes

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