Acetone → n,n'-Dimethyl-n,n'-dibutyltetradecylmalonamide

HRID 1588458Notes

Reaction equation

HRID 1588458 reaction equation
[CH3:1][N:2]([CH2:14][CH2:15][CH2:16][CH3:17])[C:3](=[O:13])[CH2:4][C:5]([N:7]([CH3:12])[CH2:8][CH2:9][CH2:10][CH3:11])=[O:6].CC(C)=O.[CH2:22](I)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35].O.C(O)C>O1CCCC1.C(Cl)Cl>[CH2:35]([CH:4]([C:3]([N:2]([CH3:1])[CH2:14][CH2:15][CH2:16][CH3:17])=[O:13])[C:5]([N:7]([CH3:12])[CH2:8][CH2:9][CH2:10][CH3:11])=[O:6])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH3:22]

Participants

7

Reactant 4

HCID 180AcetoneHCID 295071-Iodotetradecane2×HCID 13398903HCID 13398903, compoundHCID 19096565Water ethanol

Product 1

HCID 14944519n,n'-Dimethyl-n,n'-dibutyltetradecylmalonamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent5×

Procedure

Into a 1 liter reactor, scavenged by an argon stream, is introduced 0.1 mole of N,N'-dimethyl-N,N'-dibutyl-propane diamide dissolved in 400 ml of tetrahydrofuran. Cooling takes place to -50° C. with the aid of an acetone and solid carbon dioxide bath and a N-butyl lithium solution prepared from 0.1 mole of N-butyl lithium is poured into 100 ml of anhydrous tetrahydrofuran. Under the same conditions, pouring takes place of a solution of tetradecyl iodide prepared from 0.1 mole of tetradecyl iodide and 100 ml of anhydrous tetrahydrofuran. When pouring is ended, the temperature is allowed to rise to ambient temperature, followed by refluxing the tetrahydrofuran for 3 hours. It is left to cool and then hydrolyzed with a water-ethanol mixture. The tetrahydrofuran is expelled and in this way a precipitate is formed. It is taken up with methylene chloride, washed with water, the organic layer is dried and then the solvent is expelled prior to distillation.

Workup

  1. customInto a 1 liter reactor, scavenged by an argon stream
  2. temperatureCooling
  3. customto -50° C.
  4. additionUnder the same conditions, pouring
  5. additionWhen pouring
  6. customto rise to ambient temperature
  7. waitIt is left
  8. temperatureto cool
  9. customis formed
  10. washwashed with water
  11. customthe organic layer is dried
  12. distillationto distillation

Sources & evidence

ORD record
ord-6343f1c35f254f9da0d314a955a6a599
Source dataset
uspto-grants-1993_06
Patent number
US05223232

Reaction notes

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