Bromide ion → N~1~,N~3~-Dibutyl-2-(2-ethoxyethyl)-N~1~,N~3~-dimethylpropanediamide

HRID 622320Notes

Reaction equation

HRID 622320 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].C(=O)=O.C([Li])CCC.[CH2:26]([O:28][CH:29](Br)[CH3:30])[CH3:27].[Br-]>O1CCCC1.C(Cl)Cl.O.C(O)C>[CH2:26]([O:28][CH2:29][CH2:30][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])[CH3:27]

Participants

9

Reactant 5

HCID 259Bromide ionHCID 280Carbon DioxideHCID 13398903HCID 13398903, compoundHCID 145479151-Bromo-1-ethoxyethaneHCID 178418339Butyllithium2×

Product 1

HCID 13797466N~1~,N~3~-Dibutyl-2-(2-ethoxyethyl)-N~1~,N~3~-dimethylpropanediamide

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent5×HCID 19096565Water ethanolSolvent

Procedure

##STR28## 0.1 mol of N,N'-dimethyl-N,N'-dibutyl-propane diamide obtained in example 3(a) dissolved in 400 ml of anhydrous tetrahydrofuran were introduced into a one liter reactor, scavenged by an argon flow. Cooling took place to -50° C. using an acetone bath and solid carbon dioxide and pouring took 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 was prepared a solution of ethoxy-2-ethyl bromide of formula BrCH2 --CH2 --O--C2H5 prepared from 0.1 mol of bromide and 100 ml of anhydrous tetrahydrofuran. With pouring at an end, the temperature was allowed to rise to ambient temperature, followed by refluxing the tetrahydrofuran for three hours. This was followed by cooling and hydrolysis with a water-ethanol mixture. The tetrahydrofuran was expelled and a precipitate formed, followed by taking up with methylene chloride. This was followed by washing with water, drying the organic layer, expelling the solvent before performing chromatography on a silica gel column using as the eluent a mixture of ethyl acetate and cyclohexane (80:20 by volume). A yellow liquid was recovered constituted by 2-ethoxyethyl-N,N'-dimethyl-N,N'-dibutyl-propane diamide. The product was characterized by mass spectrometry, magnetic resonance of the proton and potentiometry, the eld was 40%.

Workup

  1. additionwere introduced into a one liter reactor
  2. temperatureCooling
  3. customto -50° C.
  4. additionWith pouring at an end
  5. customto rise to ambient temperature
  6. temperatureby cooling
  7. customa precipitate formed
  8. washby washing with water
  9. customdrying the organic layer
  10. additiona mixture of ethyl acetate and cyclohexane (80:20 by volume)
  11. customA yellow liquid was recovered

Sources & evidence

ORD record
ord-1093b938eba94f61853d7984e2e47379
Source dataset
uspto-grants-1988_09
Patent number
US04770807

Reaction notes

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