Sodium Hydroxide → 2-(3-isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazole-5 carboxylic acid

HRID 896303Notes

Reaction equation

HRID 896303 reaction equation
[CH:1]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([CH2:13][C:14]2[N:18]([CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])[C:17]3[CH:24]=[CH:25][C:26]([C:28]#N)=[CH:27][C:16]=3[N:15]=2)[C:5]1=[O:30])([CH3:3])[CH3:2].[OH-:31].[NH4+].[OH-:33].[Na+]>Cl>[CH:1]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([CH2:13][C:14]2[N:18]([CH2:19][CH2:20][CH:21]([CH3:22])[CH3:23])[C:17]3[CH:24]=[CH:25][C:26]([C:28]([OH:33])=[O:31])=[CH:27][C:16]=3[N:15]=2)[C:5]1=[O:30])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 14923Ammonium HydroxideHCID 223493242-(3-isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazole-5-carbonitrile

Product 1

HCID 223493412-(3-isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazole-5 carboxylic acidYield 83%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 2-(3-isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazole-5-carbonitrile (2.00 g, 5.0 mmol) and 6M HCl (50 mL) was heated to reflux for 12 h. After cooling, the final solution was neutralized by ammonium hydroxide and 1M NaOH to pH 6. The precipitate was collected by filtration and the solid washed with water thoroughly and dried in a vacuum oven to yield 1.74 g (83%) of 2-(3-isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazole-5 carboxylic acid as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 12 h
  3. temperatureAfter cooling
  4. filtrationThe precipitate was collected by filtration
  5. washthe solid washed with water thoroughly
  6. customdried in a vacuum oven

Sources & evidence

ORD record
ord-1716b42f6d964eb691b9cb4356c1f499
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

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