Acetonitrile → HCID 44442492, compound

HRID 896392Notes

Reaction equation

HRID 896392 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][CH:26]=[C:27]([CH:28]=[O:29])[C:16]=3[N:15]=2)[C:5]1=[O:30])([CH3:3])[CH3:2].Cl([O-])=O.[Na+].[OH-].[Na+].[C:37](#N)C>O>[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][CH:26]=[C:27]([CH2:28][O:29][CH3:37])[C:16]=3[N:15]=2)[C:5]1=[O:30])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 14798Sodium HydroxideHCID 22349276HCID 22349276, compoundHCID 23668197Sodium Chlorite2×

Product 1

HCID 44442492HCID 44442492, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-(3-Isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazole-4-carbaldehyde (37 mg, 0.091 mmol) and sodium chlorite (12 mg, 0.11 mmol) in water (1 mL) and acetonitrile (1 mL) was stirred at room temperature for 8 hrs. An additional amount of sodium chlorite (12 mg) was added and stirring was continued overnight. 1M NaOH was added and the mixture was extracted with ethyl acetate (twice). The aqueous phase was acidified with 1M HCl until pH 4. The resulting suspension was extracted with ethyl acetate (2×10 mL) and the combined organic phases washed with water, brine, and dried (MgSO4). The pure title compound (8 mg, 21%) was obtained as a white solid:

Workup

  1. stirringstirring
  2. waitwas continued overnight
  3. extractionthe mixture was extracted with ethyl acetate (twice)
  4. extractionThe resulting suspension was extracted with ethyl acetate (2×10 mL)
  5. washthe combined organic phases washed with water, brine
  6. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-ec52777478954dccb070e5cc7526ea1d
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

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