Dimethylmaleic anhydride → N-(4-hydroxycyclohexyl)-dimethylmaleimide

HRID 46603

Reaktionsgleichung

Reaktionsgleichung von HRID 46603
[CH3:1][C:2]1=[C:3]([CH3:9])[C:4]([O:6][C:7]1=[O:8])=O.[NH2:10][CH:11]1[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13][CH2:12]1>C(Cl)Cl>[OH:17][CH:14]1[CH2:15][CH2:16][CH:11]([N:10]2[C:4](=[O:6])[C:3]([CH3:9])=[C:2]([CH3:1])[C:7]2=[O:8])[CH2:12][CH2:13]1

Komponenten

4

Edukt 2

HCID 13010Dimethylmaleic anhydrideHCID 812934-Aminocyclohexanol

Produkt 1

HCID 20346782N-(4-hydroxycyclohexyl)-dimethylmaleimideAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

126 g (1 mol) of dimethylmaleic anhydride and 115 g (1 mol) of 4-aminocyclohexanol are warmed, whilst stirring, to 120°-125° C. (internal temperature) for 30 minutes in an oil bath. After cooling to about 20° C., the reaction product is dissolved in 500 ml of methylene chloride and the solution is extracted once with 100 ml of 1 N NaOH, whilst cooling with ice. The reaction product is then washed twice with water and dried over Na2SO4. The solvent is evaporated and the residue is recrystallized from a 1:1 mixture by volume of ethyle acetate and petroleum ether. 155 g (70% of theory) of N-(4-hydroxycyclohexyl)-dimethyl-maleimide are obtained; melting point 109°-111° C.

Aufarbeitung

  1. extractionthe solution is extracted once with 100 ml of 1 N NaOH
  2. temperaturewhilst cooling with ice
  3. washThe reaction product is then washed twice with water
  4. dry with materialdried over Na2SO4
  5. customThe solvent is evaporated
  6. customthe residue is recrystallized from a 1:1 mixture by volume of ethyle acetate and petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-eaf52a7465754a36925234705843f923
Quelldatensatz
uspto-grants-1979_11
Patentnummer
US04174326

Verknüpfte Notizen

Wird geladen…