Potassium Hydroxide → HCID 18935171, compound

HRID 3662Notes

Reaction equation

HRID 3662 reaction equation
[CH2:1]([CH:4]1[C:9](=[O:10])[CH:8]([CH2:11][CH:12]=[CH2:13])[C:7](=[O:14])[C:6]([NH:15][C:16]([C@@H:18]2[CH2:22][CH2:21][CH2:20][C@H:19]2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=O)=[C:5]1[NH2:29])[CH:2]=[CH2:3].[OH-].[K+]>C(O)C.O>[CH2:11]([CH:8]1[C:9](=[O:10])[CH:4]([CH2:1][CH:2]=[CH2:3])[C:5]2[NH:29][C:16]([CH:18]3[CH2:22][CH2:21][CH2:20][CH:19]3[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[N:15][C:6]=2[C:7]1=[O:14])[CH:12]=[CH2:13]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 70075589HCID 70075589, compound

Product 1

HCID 18935171HCID 18935171, compoundYield 52.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

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).

Workup

  1. temperatureheat
  2. customthe reaction to 60° C. for 4 hours
  3. temperatureCool
  4. customthe reaction
  5. extractionAcidify with concentrated hydrochloric acid and extract with diethyl ether (400 ml)
  6. washRinse the
  7. extractionorganic extract with water (200 ml), saturated sodium chloride (200 ml)
  8. dry with materialdry over anhydrous magnesium sulfate
  9. filtrationfilter
  10. concentrationconcentrate under vacuum
  11. customPurify the residue by radial chromatography (40% to 50% ethyl acetate/hexane, 2 mm plate)

Sources & evidence

ORD record
ord-c8fa4707b7f14f039824c58e9cb46488
Source dataset
uspto-grants-1998_03
Patent number
US05734052

Reaction notes

Loading…