Reaktion #3758

Reaktionsgleichung

trans-2-phenylcyclopentanecarboxylic acid (3,5-diallyl-2-amino-4,6-dioxo-cyclohex-1-enyl)amide

potassium hydroxide

→

5,7-diallyl-2-(2-phenylcyclopentyl)-1,7-dihydrobenzoimidazole-4,6-dione

Ausbeute 52.4%

Lösungsmittel

water

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheat
2. 2
   Sonstigethe reaction to 60° C. for 4 hours
3. 3
   TemperaturCool
4. 4
   Sonstigethe reaction
5. 5
   ExtraktionAcidify with concentrated hydrochloric acid and extract with diethyl ether (400 ml)
6. 6
   WaschenRinse the
7. 7
   Extraktionorganic extract with water (200 ml), saturated sodium chloride (200 ml)
8. 8
   Trocknendry over anhydrous magnesium sulfate
9. 9
   Filtrationfilter
10. 10
    Einengenconcentrate under vacuum
11. 11
    SonstigePurify the residue by radial chromatography (40% to 50% ethyl acetate/hexane, 2 mm plate)

Vorschrift

Dissolve trans-2-phenylcyclopentanecarboxylic acid (3,5-diallyl-2-amino-4,6-dioxo-cyclohex-1-enyl)amide (300 mg, 0.76 mmol) in ethanol (100 ml), add 10% potassium hydroxide (100 ml) and heat the reaction to 60° C. for 4 hours. Cool the reaction and dilute with water (200 ml). Acidify with concentrated hydrochloric acid and extract with diethyl ether (400 ml). Rinse the organic extract with water (200 ml), saturated sodium chloride (200 ml), dry over anhydrous magnesium sulfate, filter and concentrate under vacuum. Purify the residue by radial chromatography (40% to 50% ethyl acetate/hexane, 2 mm plate) to provide 5,7-diallyl-2-(2-phenylcyclopentyl)-1,7-dihydrobenzoimidazole-4,6-dione (149 mg).

Quelle