Triethylamine → N-(2,3-dimethylnaphthyl)-N-(2-oxo-tetrahydrofuran-3-yl)-N-(2-methoxy-ethoxy-acetyl)-amine

HRID 653694

Reaktionsgleichung

Reaktionsgleichung von HRID 653694
[CH3:1][C:2]1[C:11]([CH3:12])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[NH:13][CH:14]1[CH2:18][CH2:17][O:16][C:15]1=[O:19].[CH3:20][O:21][CH2:22][CH2:23][O:24][CH2:25][C:26](Cl)=[O:27].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:1][C:2]1[C:11]([CH3:12])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[N:13]([CH:14]1[CH2:18][CH2:17][O:16][C:15]1=[O:19])[C:26](=[O:27])[CH2:25][O:24][CH2:23][CH2:22][O:21][CH3:20]

Komponenten

5

Edukt 3

HCID 8471Triethylamine2×HCID 70103382-(2-Methoxyethoxy)acetyl chloride3×HCID 13092367N-(2,3-dimethylnaphtyl)-N-(2-oxo-tetrahydrofuran-3-yl)-amine

Produkt 1

HCID 67917313N-(2,3-dimethylnaphthyl)-N-(2-oxo-tetrahydrofuran-3-yl)-N-(2-methoxy-ethoxy-acetyl)-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel3×

Versuchsvorschrift

To 15.3 g of N-(2,3-dimethylnaphtyl)-N-(2-oxo-tetrahydrofuran-3-yl)-amine in 120 ml of toluene are added dropwise 12.2 g of 2-methoxyethoxy-acetyl chloride (MAC) in 20 ml of toluene and afterwards 8.1 g of triethylamine in 20 ml of toluene. The temperature of the reaction rises to 35° and is then raised to 40° for 2 hours. There are subsequently added dropwise a further 2 g of MAC and 1.5 g of triethylamine. The temperature is held overnight at 40°, and afterwards a further 2 g of MAC are added dropwise. After 4 hours, the reaction mixture is cooled to room temperature and filtered, and the filtrate is concentrated by evaporation to yield a resinous residue, which is purified through silica gel 60 using ethyl acetate as the eluant. The solid product occurring from the residue is recrystallised from isopropanol with the addition of active charcoal. The resulting product is the colourless diastereoisomeric mixture of the compound No. 32, m.p. 142°-146°.

Aufarbeitung

  1. customrises to 35°
  2. temperatureis then raised to 40° for 2 hours
  3. waitAfter 4 hours
  4. filtrationfiltered
  5. concentrationthe filtrate is concentrated by evaporation
  6. customto yield a resinous residue, which
  7. customis purified through silica gel 60 using ethyl acetate as the eluant
  8. customis recrystallised from isopropanol with the addition of active charcoal
  9. additionthe colourless diastereoisomeric mixture of the compound No

Quellen und Nachweise

ORD-Eintrag
ord-c433676cfe3a49bcbd1730250bdf12da
Quelldatensatz
uspto-grants-1992_07
Patentnummer
US05128371

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