Triethylamine → 5-Ethylpicolinonitrile

HRID 1650335Notes

Reaction equation

HRID 1650335 reaction equation
CN(C)[CH:3]=[CH:4][C:5]([NH:7][CH3:8])=[CH2:6].Cl[C:11](=[CH2:14])[C:12]#N.C([N:17](CC)CC)C>C(#N)C>[CH2:11]([C:14]1[CH:3]=[CH:4][C:5]([C:6]#[N:17])=[N:7][CH:8]=1)[CH3:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 701982-ChloroacrylonitrileHCID 867439001-Dimethylamino-1-aza-3-ethyl-1,3-butadiene

Product 1

HCID 114463525-Ethylpicolinonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

39.3 g of 1-dimethylamino-1-aza-3-ethyl-1,3-butadiene, 35 g of 2-chloroacrylonitrile and 112 ml of triethylamine are stirred in 400 ml of acetonitrile for 7 hours at 70° C. The brown reaction mixture is cooled and then filtered and concentrated by evaporation. The residue is dissolved in dioxane and gaseous HCl is introduced. The batch is stirred for 1 hour at room temperature, then concentrated by evaporation, and the residue is partitioned between chloroform and 2N sodium carbonate solution. The organic phase is separated, dried and concentrated by evaporation. The oily residue is distilled under a high vacuum, affording 30.6 g of a yellowish oil with a boiling point of 75°-79° C./3·10-1 mbar.

Workup

  1. temperatureThe brown reaction mixture is cooled
  2. filtrationfiltered
  3. concentrationconcentrated by evaporation
  4. dissolutionThe residue is dissolved in dioxane
  5. additiongaseous HCl is introduced
  6. concentrationconcentrated by evaporation
  7. customthe residue is partitioned between chloroform and 2N sodium carbonate solution
  8. customThe organic phase is separated
  9. customdried
  10. concentrationconcentrated by evaporation
  11. distillationThe oily residue is distilled under a high vacuum

Sources & evidence

ORD record
ord-4241034955a243e6b134ff8d2187dd23
Source dataset
uspto-grants-1990_05
Patent number
US04923993

Reaction notes

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