Triethylamine → 3-{beta-(1-Ethyl-2-phenylimidazole-4-yl)acryloyl}amino-delta-valerolactam

HRID 465349Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 465349
Cl.[CH2:2]([N:4]1[CH:8]=[C:7]([CH:9]=[CH:10][C:11]([OH:13])=O)[N:6]=[C:5]1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:3].C(N(CC)CC)C.[NH2:27][CH:28]1[CH2:34][CH2:33][NH:32][C:30](=[O:31])[CH2:29]1.C(=O)(O)[O-].[Na+]>S(Cl)(Cl)=O.O1CCCC1>[CH2:2]([N:4]1[CH:8]=[C:7]([CH:9]=[CH:10][C:11]([NH:27][CH:28]2[CH2:34][CH2:33][NH:32][C:30](=[O:31])[CH2:29]2)=[O:13])[N:6]=[C:5]1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:3]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 199802604-Aminopiperidin-2-oneHCID 70344434beta-(1-Ethyl-2-phenylimidazole-4-yl)acrylate hydrochloride

Produkt 1

HCID 545002753-{beta-(1-Ethyl-2-phenylimidazole-4-yl)acryloyl}amino-delta-valerolactamAusbeute 422,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 24386Thionyl ChlorideLösungsmittel2×

Versuchsvorschrift

β-(1-Ethyl-2-phenylimidazole-4-yl)acrylate hydrochloride (5.49 g, 20.3 mmole) was heated with stirring in thionyl chloride (50 ml) for 50 minutes. After excessive thionyl chloride was completely distilled off under reduced pressure, tetrahydrofuran (50 ml) and triethylamine (4.12 g, 40.7 mmole) were added and then 3-amino-δ-valerolactam (2.79 g, 24.4 mmole) was added to the mixture with cooling, followed by stirring at room temperature overnight. A sodium bicarbonate solution was added to the reaction mixture which was extracted with a chlorofolm-methanol mixed solvent. After drying over magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was subjected to silica gel flash chromatography to obtain the titled compound (29 g, 62.3%).

Aufarbeitung

  1. additionwere added
  2. temperaturewith cooling
  3. extractionwas extracted with a chlorofolm-methanol mixed solvent
  4. dry with materialAfter drying over magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9afc9657b35444d38a2628ef6d566be9
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05153201

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