Methyl chloroformate → N-(Methoxycarbonyl)maleimide

HRID 383196

Reaktionsgleichung

Reaktionsgleichung von HRID 383196
[CH3:1][O:2][C:3](Cl)=[O:4].[C:6]1(=[O:12])[NH:10][C:9](=[O:11])[CH:8]=[CH:7]1.CN1CCOCC1>CCOC(C)=O>[CH3:1][O:2][C:3]([N:10]1[C:6](=[O:12])[CH:7]=[CH:8][C:9]1=[O:11])=[O:4]

Komponenten

5

Edukt 3

HCID 6586Methyl chloroformateHCID 79724-MethylmorpholineHCID 10935Maleimide

Produkt 1

HCID 580610N-(Methoxycarbonyl)maleimideAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Methylchloroformate (4.4 mL, 56.7 mmol, 1 eq) was added to a solution of maleimide (5.5 g, 56.7 mmol, 1 eq) and NMM (6.2 mL, 56.7 mmol, 1 eq) in 200 mL of EtOAc at 0° C. The suspension was stirred at 0° C. for 30 minutes, filtered and washed with EtOAc. Filtrate and washings were combined and washed with cold water and dried over anhydrous Na2SO4. After filtration and evaporation under vacuum a pink solid was obtained. Purification by column chromatography on silica gel (Hexane-EtOAc, 1:1, v/v) provided the product (4.8 g, 55%).

Aufarbeitung

  1. filtrationfiltered
  2. washwashed with EtOAc
  3. washwashed with cold water
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationAfter filtration and evaporation under vacuum a pink solid
  6. customwas obtained
  7. customPurification by column chromatography on silica gel (Hexane-EtOAc, 1:1

Quellen und Nachweise

ORD-Eintrag
ord-f1acf67d1cd44f2980ceb3ef2322c62b
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367065B2

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