Triethylamine → N-(3-Methacrylamidopropyl)-3-oxobutanamide

HRID 67744

Reaktionsgleichung

Reaktionsgleichung von HRID 67744
C(N(CC)CC)C.Cl.[NH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14](=[O:18])[C:15]([CH3:17])=[CH2:16].[CH2:19]=[C:20]1[O:24][C:22](=[O:23])[CH2:21]1>CO>[C:22]([NH:9][CH2:10][CH2:11][CH2:12][NH:13][C:14](=[O:18])[C:15]([CH3:17])=[CH2:16])(=[O:23])[CH2:21][C:20]([CH3:19])=[O:24]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 12661DiketeneHCID 103750052-Propenamide, N-(3-aminopropyl)-2-methyl-, hydrochloride (1:1)

Produkt 1

HCID 23223314N-(3-Methacrylamidopropyl)-3-oxobutanamideAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Triethylamine (24 g, 0.24 mole) was added dropwise at 0° C. to a solution of N-(3-aminopropyl)-methacrylamide hydrochloride (40 g, 0.24 mole) and diketene (20 g, 0.24 mole) in methanol (800 ml). After addition, the temperature was maintained at 0° C. for 2 hours under stirring. Stirring was continued at 20° C. for 20 hours. The solvent was then removed. The residue was dissolved in chloroform (1 liter), washed with 5% hydrochloric acid (200 ml), washed with saturated NaHCO3 (200 ml), dried over anhydrous magnesium sulfate, and filtered. Excess solvent was removed. The residue was recrystallized from benzene (500 ml) and ethyl ether (500 ml) to give N-(3-acetoacetamidopropyl)methacrylamide (m.p.=93°-94° C.) at a yield of 50%.

Aufarbeitung

  1. additionAfter addition
  2. stirringStirring
  3. customThe solvent was then removed
  4. dissolutionThe residue was dissolved in chloroform (1 liter)
  5. washwashed with 5% hydrochloric acid (200 ml)
  6. washwashed with saturated NaHCO3 (200 ml)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customExcess solvent was removed
  10. customThe residue was recrystallized from benzene (500 ml) and ethyl ether (500 ml)

Quellen und Nachweise

ORD-Eintrag
ord-b568e52c429c41d884e4a5fac2e5a3f6
Quelldatensatz
uspto-grants-1982_08
Patentnummer
US04346231

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