4-Nitrobenzaldehyde → HCID 18472662, Verbindung

HRID 566062

Reaktionsgleichung

Reaktionsgleichung von HRID 566062
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.[CH3:13][O:14][C:15](=[O:19])[CH2:16][NH:17][CH3:18].C(N(CC)CC)C.O>ClCCCl>[CH3:13][O:14][C:15](=[O:19])[CH2:16][N:17]([CH2:8][C:7]1[CH:10]=[CH:11][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)[CH3:18]

Komponenten

6

Edukt 4

HCID 5414-NitrobenzaldehydeHCID 962WaterHCID 8471TriethylamineHCID 83544Glycine, N-methyl-, methyl ester, hydrochloride (1:1)

Produkt 1

HCID 18472662HCID 18472662, VerbindungAusbeute 80,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

In 1,2-dichloroethane (50 ml) were suspended p-nitrobenzaldehyde (5 g), sarcosine methyl ester hydrochloride (4.6 g) and triethylamine (4.6 ml), and to the mixture was added, under ice-cooling, triacetoxy sodium boron hydride (9.8 g). Under nitrogen atmosphere, the mixture was stirred at room temperature for 4 hours. To the mixture was added water, and the mixture was concentrated, neutralized with sodium hydroxide solution and extracted with ethyl acetate. The organic layer was washed with water and brine, and dried with anhydrous magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column (ethyl acetate/hexane) to give N-(4-nitrobenzyl)sarcosine methyl ester (6.3 g) as colorless oil.

Aufarbeitung

  1. additionto the mixture was added, under ice-
  2. temperaturecooling
  3. concentrationthe mixture was concentrated
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customUnder reduced pressure, the solvent was evaporated
  8. customthe residue was purified with silica gel column (ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-ec5112c45ac9435d8695ad166943129b
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06172061B2

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