Carbon Dioxide → 2-hexyl-N,N'-dimethyl-N,N'-dibutyl-propane diamide

HRID 622319Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 622319
[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].C(=O)=O.C([Li])CCC.[CH2:26](I)[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]>O1CCCC1.C(Cl)Cl.O.C(O)C>[CH2:26]([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])[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Komponenten

8

Edukt 4

HCID 280Carbon DioxideHCID 125271-Iodohexane2×HCID 13398903N1,N3-dibutyl-N1,N3-dimethylmalonamideHCID 178418339Butyllithium2×

Produkt 1

HCID 137974652-hexyl-N,N'-dimethyl-N,N'-dibutyl-propane diamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel5×HCID 19096565Water ethanolLösungsmittel

Versuchsvorschrift

Preparation of 2-hexyl-N-N'-dimethyl-N,N'-dibutyl-propane diamide of formula: ##STR27## 0.1 mol of N,N'-dimethyl-N,N'-dibutyl-propane diamide dissolved in 400 ml of tetrahydrofuran are introduced into a one liter reactor, scavenged by a nitrogen stream. Cooling takes place to -50° C. using an acetone bath and solid carbon dioxide and pouring takes place of a solution of n-butyl lithium prepared from 0.1 mol of n-butyl lithium in 100 ml of anhydrous tetrahydrofuran. Under the same conditions is poured a solution of hexyl iodide prepared from 0.1 mol of hexyl iodide and 100 ml of anhydrous tetrahydrofuran. When pouring is at an end, the temperature is allowed to rise to ambient temperature again, followed by refluxing the tetrahydrofuran for three hours. Cooling is allowed to take place, followed by hydrolysis with a water-ethanol mixture. The tetrahydrofuran is expelled and in this way a precipitate is formed. This is taken up with methylene chloride, followed by washing with water, drying the organic layer, expelling the solvent and then distillation. The boiling point is 145° to 148° C. under 0.4 mm of mercury and the product is a yellow liquid. Its characterization by nuclear magnetic resonance of the proton and by potentiometric dosage confirms that it corresponds to the above formula.

Aufarbeitung

  1. additionare introduced into a one liter reactor
  2. temperatureCooling
  3. customto -50° C.
  4. additionWhen pouring
  5. customto rise to ambient temperature
  6. temperatureCooling
  7. customis formed
  8. washby washing with water
  9. customdrying the organic layer
  10. distillationdistillation

Quellen und Nachweise

ORD-Eintrag
ord-abd3c34c517b4687abba1ba9b86a929d
Quelldatensatz
uspto-grants-1988_09
Patentnummer
US04770807

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