반응 #3758

반응 방정식

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

수율 52.4%

용매

water

ethanol

반응 조건

후처리

1. 1
   온도heat
2. 2
   기타the reaction to 60° C. for 4 hours
3. 3
   온도Cool
4. 4
   기타the reaction
5. 5
   추출Acidify with concentrated hydrochloric acid and extract with diethyl ether (400 ml)
6. 6
   세척Rinse the
7. 7
   추출organic extract with water (200 ml), saturated sodium chloride (200 ml)
8. 8
   건조dry over anhydrous magnesium sulfate
9. 9
   여과filter
10. 10
    농축concentrate under vacuum
11. 11
    기타Purify the residue by radial chromatography (40% to 50% ethyl acetate/hexane, 2 mm plate)

실험 절차

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).

출처