Potassium Hydroxide → HCID 19383088, compound

HRID 2399687Notes

Reaction equation

HRID 2399687 reaction equation
[CH2:1]([C:4]1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH2:20][CH2:19][CH2:18][C:17]=3[C:21]([O:23]C)=[O:22])=[CH:12][CH:11]=2)[C:7]2[CH:25]=[CH:26][CH:27]=[CH:28][C:6]=2[N:5]=1)[CH2:2][CH3:3].[OH-].[K+]>O1CCOCC1>[CH2:1]([C:4]1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH2:20][CH2:19][CH2:18][C:17]=3[C:21]([OH:23])=[O:22])=[CH:12][CH:11]=2)[C:7]2[CH:25]=[CH:26][CH:27]=[CH:28][C:6]=2[N:5]=1)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 19383102HCID 19383102, compound

Product 1

HCID 19383088HCID 19383088, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of methyl 2-[4-[(2-propyl-1H-benzimidazol-1-yl)methyl]phenyl]-1-cyclopentene-1-carboxylate (1.60 g, 4.27 mmol), 1N KOH (8.5 mL), and dioxane (8.5 mL) was heated under reflux for 1 h. The mixture was concentrated, diluted with water (10 mL), and extracted with ether (discarded). The aqueous phase was neutralized with 1N HCl (8.5 mL) and the white precipitate was collected by filtration. Trituration with EtOH gave 1.04 g (68%) of product, mp 224°-226° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 h
  3. concentrationThe mixture was concentrated
  4. additiondiluted with water (10 mL)
  5. extractionextracted with ether (discarded)
  6. filtrationthe white precipitate was collected by filtration

Sources & evidence

ORD record
ord-487a344f096e43de9615511fc824cf48
Source dataset
uspto-grants-1995_09
Patent number
US05451583

Reaction notes

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