HCID 53767790, compound → HCID 21468837, compound

HRID 743877Notes

Reaction equation

HRID 743877 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-fef004529c7c42649d72ab733723e7c9
Source dataset
uspto-grants-1996_09
Patent number
US05556981

Reaction notes

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