2-Oxazolidinone → 1-(3-Nitrophenyl)imidazolidin-2-one

HRID 235993

Reaktionsgleichung

Reaktionsgleichung von HRID 235993
[N+:1]([C:4]1[CH:5]=[C:6]([N:10]=[C:11]=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].O1[CH2:17][CH2:16][NH:15]C1=O.[Al+3].[Cl-].[Cl-].[Cl-]>ClCCl>[N+:1]([C:4]1[CH:5]=[C:6]([N:10]2[CH2:17][CH2:16][NH:15][C:11]2=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Komponenten

5

Edukt 3

HCID 739492-OxazolidinoneHCID 768353-Nitrophenyl isocyanateHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 2867471-(3-Nitrophenyl)imidazolidin-2-oneAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
195 °C

Versuchsvorschrift

A mixture of 3-nitrophenyl isocyanate (50 mmoles), 2-oxazolidinone (50 mmoles) and anhydrous AlCl3 (40 mg, 0.3 mmole) is heated at 195° C. for 6 hours with stirring. The reaction mixture is dissolved in dichloromethane and the resulting solution is washed with water twice. The dichloromethane solution is dried and evaporated and the residue distilled at reduced pressure. The distillate is recrystallized from hot hexane to give a yield of 33 percent of the desired product, m.p. 158° C-160° C.

Aufarbeitung

  1. washthe resulting solution is washed with water twice
  2. dry with materialThe dichloromethane solution is dried
  3. customevaporated
  4. distillationthe residue distilled at reduced pressure
  5. customThe distillate is recrystallized from hot hexane

Quellen und Nachweise

ORD-Eintrag
ord-ecaaf6db826c419e83353326088cc88f
Quelldatensatz
uspto-grants-1987_02
Patentnummer
US04642351

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