Reaktion #440556

Reaktionsgleichung

ethanol

3-oxo-tricyclo[2.2.1.02,6]heptane-1-carboxylic acid

potassium cyanide

ammonium carbonate

potassium cyanide

ammonium carbonate

→

title compound

2′,5′-Dioxo-spiro{tricyclo[2.2.1.02,6]heptane-3,4′-imidazoline}-1-carboxylic acid

Lösungsmittel

ethanol water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirring at 75° C.
2. 2
   workup.WAITwas continued for 18 hours
3. 3
   Sonstigeto evaporate
4. 4
   TemperaturUpon cooling the mixture to 0° C.
5. 5
   Sonstigea white precipitate formed
6. 6
   Sonstigewas removed by filtration
7. 7
   Waschenwashed with ice-cold water and ethyl acetate
8. 8
   Sonstigedried in vacuum

Vorschrift

A mixture of 1.52 g (10 mmole) of 3-oxo-tricyclo[2.2.1.02,6]heptane-1-carboxylic acid, 0.78 g (12 mmole) of potassium cyanide and 3.36 g (35 mmole) of ammonium carbonate in 75 mL of ethanol-water (1:1) was stirred at 75° C. for 18 hours. An additional 2-4 mmole of potassium cyanide and 6-12 mmole of ammonium carbonate were added and stirring at 75° C. was continued for 18 hours. The ethanol was then allowed to evaporate and the reaction mixture adjusted to pH 1 with concentrated HCl. Upon cooling the mixture to 0° C., a white precipitate formed and was removed by filtration and washed with ice-cold water and ethyl acetate and dried in vacuum to give 1.32 g of the title compound. Concentration of the mother liquor led to the isolation of an additional 0.22 g of white solid. Thus, 1.54 g of the title compound were obtained as a mixture of diastereomers.

Quelle