N-Ethylmaleimide → 2-Azido-n-ethylsuccinimide

HRID 1760762Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1760762
[CH2:1]([N:3]1[C:7](=[O:8])[CH:6]=[CH:5][C:4]1=[O:9])[CH3:2].[NH:10]=[N+:11]=[N-:12].C1(=O)NC(=O)C=C1>C1(C)C=CC=CC=1>[N:10]([CH:5]1[CH2:6][C:7](=[O:8])[N:3]([CH2:1][CH3:2])[C:4]1=[O:9])=[N+:11]=[N-:12]

Komponenten

5

Edukt 3

HCID 4362N-EthylmaleimideHCID 10935Maleimide2×HCID 24530Hydrazoic acid

Produkt 1

HCID 101763002-Azido-n-ethylsuccinimideAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
-30 °C

Versuchsvorschrift

A solution in toluene of N-ethylmaleimide, HN3 (excess relative to the maleimide), and the (salen)AlN3 catalyst depicted above (10 mol % relative to the maleimide) was maintained at −30° C. for 18 h. After a standard quench and work-up of the reaction mixture, the crude material was purified to yield 2-azido-N-ethylsuccinimide (93%, 93% ee).

Aufarbeitung

  1. customAfter a standard quench
  2. customwork-up of the reaction mixture, the crude material was purified

Quellen und Nachweise

ORD-Eintrag
ord-109b039de3c44ae48d6086c1d83667e9
Quelldatensatz
uspto-grants-2005_01
Patentnummer
US06844448B2

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