Triethylamine → 3541-31-9

HRID 991855Notes

Reaction equation

HRID 991855 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][CH2:6][C:5]1=[O:9].C(N(CC)CC)C.[C:17](Cl)(=[O:20])[CH:18]=[CH2:19]>C(Cl)(Cl)Cl>[C:17]([O:1][CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][CH2:6][C:5]1=[O:9])(=[O:20])[CH:18]=[CH2:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 769801-(2-Hydroxyethyl)-2-pyrrolidinone

Product 1

HCID 109869433541-31-9Yield 70%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Into a solution of 50 mL of 1-(2-hydroxyethyl)-2-pyrrolidone and 85 mL of triethylamine in 150 mL of chloroform, a solution of 50 mL of acryloyl chloride in 100 mL of chloroform was dropped over 2 hours with stirring. The reaction mixture was stirred at 4° C. for 20 hours, then at 50° C. for 2 hours. After being cooled, the solution was filtered and the filtrate was washed with a 15% aqueous sodium carbonate solution and then concentrated under vacuum. The obtained oily material was distilled under vacuum to give the title compound in a yield of 70%.

Workup

  1. stirringThe reaction mixture was stirred at 4° C. for 20 hours
  2. temperatureAfter being cooled
  3. filtrationthe solution was filtered
  4. washthe filtrate was washed with a 15% aqueous sodium carbonate solution
  5. concentrationconcentrated under vacuum
  6. distillationThe obtained oily material was distilled under vacuum

Sources & evidence

ORD record
ord-bdd0c9addc894307a672f10ea169092a
Source dataset
uspto-grants-2002_10
Patent number
US06465588B1

Reaction notes

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