Sodium Hydroxide → 4-(2-Oxo-2,3-dihydro-1H-benzimidazol-1-yl)butanoic acid

HRID 1381098Notes

Reaction equation

HRID 1381098 reaction equation
[O:1]=[C:2]1[N:6]([CH2:7][CH2:8][CH2:9][C:10]([O:12]CC)=[O:11])[C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=2[NH:3]1.[OH-].[Na+]>CO>[O:1]=[C:2]1[N:6]([CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])[C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=2[NH:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 103997611H-Benzimidazole-1-butanoic acid, 2,3-dihydro-2-oxo-, ethyl ester

Product 1

HCID 132517844-(2-Oxo-2,3-dihydro-1H-benzimidazol-1-yl)butanoic acidYield 92.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 22 g of the product of Step B, 22 ml of sodium hydroxide solution and 200 ml of methanol was refluxed for one hour and the methanol was evaporated. The residue was taken up in 1.5 liters of iced water and the pH was adjusted to 1 by addition of concentrated hydrochloric acid. The mixture was vacuum filtered and the product was washed with water to obtain 18.1 g of 2,3-dihydro-2-oxo-1H-benzimidazol-1-butanoic acid melting at 180° C. The product was crystallized from isopropanol to obtain 15.2 g of product melting at 185° C.

Workup

  1. customthe methanol was evaporated
  2. additionthe pH was adjusted to 1 by addition of concentrated hydrochloric acid
  3. filtrationfiltered
  4. washthe product was washed with water

Sources & evidence

ORD record
ord-94f44e8a2dd0406187b2a315f4518f5e
Source dataset
uspto-grants-1986_04
Patent number
US04585770

Reaction notes

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