Dichloromethane → (9Z)-N,N-Diethyl-9-octadecenamide

HRID 2261411Notes

Reaction equation

HRID 2261411 reaction equation
C(Cl)(=O)C(Cl)=O.C(Cl)Cl.[C:10]([OH:29])(=O)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]/[CH:18]=[CH:19]\[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].[CH2:30]([NH:32][CH2:33][CH3:34])[CH3:31]>O>[CH2:30]([N:32]([CH2:33][CH3:34])[C:10](=[O:29])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]/[CH:18]=[CH:19]\[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH3:31]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8021DiethylamineHCID 65578Oxalyl chlorideHCID 445639Oleic Acid

Product 1

HCID 6197971(9Z)-N,N-Diethyl-9-octadecenamideYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a nitrogen atmosphere, oxalyl chloride (0.46 mL, 5.4 mmol) was dropped into an absolute methylene chloride solution (8.5 mL) of oleic acid (503 mg, 1.8 mmol) under ice cooling. The solution was then stirred at room temperature for four hours. Thereafter it was concentrated under reduced pressure. Diethylamine (1.0 mL, 9.7 mmol) was added to the resultant residue, which was then stirred at room temperature for 0.5 hour. Water was then added, and extraction was performed with ethyl acetate. The organic layer thus obtained was washed with saturated saline, dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The crude extract thus obtained was purified using column chromatography (n-hexane:ethyl acetate=1:2). Thus (Z)-N,N-diethyl-9-octadecenamide (495 mg, 82%) was obtained as a colorless oily matter.

Workup

  1. concentrationThereafter it was concentrated under reduced pressure
  2. stirringwas then stirred at room temperature for 0.5 hour
  3. extractionextraction
  4. customThe organic layer thus obtained
  5. washwas washed with saturated saline
  6. dry with materialdried with anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. extractionThe crude extract thus
  9. customobtained
  10. customwas purified

Sources & evidence

ORD record
ord-6dfd18290b0446dea97eeafb7aba85fb
Source dataset
uspto-grants-2010_12
Patent number
US07846972B2

Reaction notes

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