HCID 53767790, compound → HCID 21468837, compound

HRID 976573Notes

Reaction equation

HRID 976573 reaction equation
N1C=CC=CC=1CC[O:9][C:10](=[O:35])[CH:11]([N:18]1[C:22]2[CH:23]=[CH:24][C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]#[N:34])=[CH:26][C:21]=2[N:20]=[CH:19]1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]>CO.[OH-].[Na+]>[C:33]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[C:25]1[CH:24]=[CH:23][C:22]2[N:18]([CH:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:10]([OH:35])=[O:9])[CH:19]=[N:20][C:21]=2[CH:26]=1)#[N:34]

Participants

4

Reactant 1

HCID 53767790HCID 53767790, compound

Product 1

HCID 21468837HCID 21468837, compoundYield 85.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

2-[5-(2-Cyanophenyl)-1H-benzimidazol-1-yl]octanoic acid 2-pyridylethylester (0.042 moles, 19.6 g) was dissolved in 20 ml of methanol and 8 ml of 1N NaOH. The solution was stirred at room temperature for 3 hours. The reaction was concentrated under vacuum, dissolved in water, and washed with ether. The pH was adjusted to 3.0 with 5N HCl. The intermediate was extracted with ethyl acetate. The organic phase was washed with brine, dried over sodium sulfate, and concentrated. The reaction produced 13.0 g of 2-[5-(2-cyanophenyl)-1H-benzimidazol-1-yl]octanoic acid. (MS).

Workup

  1. concentrationThe reaction was concentrated under vacuum
  2. dissolutiondissolved in water
  3. washwashed with ether
  4. extractionThe intermediate was extracted with ethyl acetate
  5. washThe organic phase was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5337ac91accd4149837300ebdaf5297a
Source dataset
uspto-grants-1997_03
Patent number
US05612360

Reaction notes

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