Pyridine → 2-[(3-Oxobutanoyl)amino]ethyl 2-methylprop-2-enoate

HRID 905104

Reaktionsgleichung

Reaktionsgleichung von HRID 905104
N1C=CC=CC=1.Cl.[C:8]([O:13][CH2:14][CH2:15][NH2:16])(=[O:12])[C:9]([CH3:11])=[CH2:10].[CH2:17]=[C:18]1[O:22][C:20](=[O:21])[CH2:19]1>CN(C)C=O>[C:8]([O:13][CH2:14][CH2:15][NH:16][C:20](=[O:21])[CH2:19][C:18]([CH3:17])=[O:22])(=[O:12])[C:9]([CH3:11])=[CH2:10]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 12661DiketeneHCID 75495Aminoethyl methacrylate hydrochloride

Produkt 1

HCID 220239722-[(3-Oxobutanoyl)amino]ethyl 2-methylprop-2-enoateAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

Pyridine (16 g, 0.2 mole) was added dropwise at 0° C. to a solution of 2-aminoethyl methacrylate hydrochloride (33 g, 0.2 mole) and diketene (16.8 g, 0.2 mole) in N,N-dimethylformamide (600 ml). After the addition, the solution was stirred at 20° C. for 20 hours. The solvent was then removed at low vacuum. The residue was dissolved in chloroform (1200 ml), washed with water (twice with 200 ml), dried over anhydrous magnesium sulfate and filtered. Excess solvent was then removed. Distillation of the residue gave acetoacetamidoethyl methacrylate (b.p.=113°-132° C./5μ) at a yield of 60%.

Aufarbeitung

  1. additionAfter the addition
  2. customThe solvent was then removed at low vacuum
  3. dissolutionThe residue was dissolved in chloroform (1200 ml)
  4. washwashed with water (twice with 200 ml),
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customExcess solvent was then removed
  8. distillationDistillation of the residue

Quellen und Nachweise

ORD-Eintrag
ord-4af832bd7cb74f51a2e5b5031ea5f5d0
Quelldatensatz
uspto-grants-1983_12
Patentnummer
US04421915

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