Triethylamine → 2-[beta-(2-furyl)acrylamido]-N5-methyl-N1,N1-di(n-propyl)pentane-1,5-diamide

HRID 64925

Reaktionsgleichung

Reaktionsgleichung von HRID 64925
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[CH:7][C:8]([OH:10])=O.C(N(CC)CC)C.C(Cl)(=O)OCC.Cl.[NH2:25][CH:26]([CH2:36][CH2:37][C:38]([NH:40][CH3:41])=[O:39])[C:27]([N:29]([CH2:33][CH2:34][CH3:35])[CH2:30][CH2:31][CH3:32])=[O:28]>C(Cl)Cl>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[CH:7][C:8]([NH:25][CH:26]([CH2:36][CH2:37][C:38]([NH:40][CH3:41])=[O:39])[C:27]([N:29]([CH2:30][CH2:31][CH3:32])[CH2:33][CH2:34][CH3:35])=[O:28])=[O:10]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 10876Furylacrylic acidHCID 10928Ethyl chloroformateHCID 86740989HCID 86740989, Verbindung

Produkt 1

HCID 867409902-[beta-(2-furyl)acrylamido]-N5-methyl-N1,N1-di(n-propyl)pentane-1,5-diamideAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

In 75 ml of methylene chloride was dissolved 1.5 g of β-(2-furyl)acrylic acid, and 2.7 g of triethylamine and 1.3 g of ethyl chlorocarbonate were successively added thereto dropwise at -25° C. to -20° C. After 30 minutes, 3 g of the DL-2-amino-N5 -methyl-N1,N1 -di(n-propyl)-pentane-1,5-diamide hydrochloride was added to the above solution, and the resulting mixture was subjected to reaction at the same temperature for 30 minutes and at room temperature for 30 minutes. After completion of the reaction, the reaction mixture was washed successively with 30 ml of a 5% aqueous sodium hydroxide solution, 30 ml of diluted hydrochloric acid and 30 ml of water and then dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure to obtain 3.1 g (yield 80%) of DL-2-[β-(2-furyl)acrylamido]-N5 -methyl-N1,N1 -di(n-propyl)pentane-1,5-diamide having a melting point of 112°-113° C.

Aufarbeitung

  1. additionwere successively added
  2. customdropwise at -25° C. to -20° C
  3. customthe resulting mixture was subjected to reaction at the same temperature for 30 minutes and at room temperature for 30 minutes
  4. customAfter completion of the reaction
  5. washthe reaction mixture was washed successively with 30 ml of a 5% aqueous sodium hydroxide solution, 30 ml of diluted hydrochloric acid and 30 ml of water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed by distillation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-47a1a8fa8c3e452ea1b4ee37c4296f87
Quelldatensatz
uspto-grants-1986_09
Patentnummer
US04610983

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