Benzophenone → Benzimidazole

HRID 730327

Reaction equation

HRID 730327 reaction equation
S(=O)(=O)(O)O.[NH2:6][CH2:7][C:8]#[N:9].[C:10]([C:18]1C=CC=CC=1)(=O)[C:11]1C=CC=C[CH:12]=1.[CH3:24]CN(C(C)C)C(C)C>ClCCl>[N:9]1[C:8]2[CH:18]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][CH:24]=1

Participants

5

Reactant 3

HCID 3102BenzophenoneHCID 81531DiisopropylethylamineHCID 196971Aminoacetonitrile sulfate (1:1)

Product 1

HCID 5798BenzimidazoleYield 156,273.703%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-aminoacetonitrile bisulfate (2.9 g, 0.013 mmol) in dichloromethane (50 mL) was added benzophenone (3.48 mL, 0.0208 mmol) followed by DIEA (4.53 mL, 0.026 mmol). After stirring 18 h, the dichloromethane solution was washed with water (50 mL), dried over sodium sulfate, filtered, and the filtrate concentrated under reduced pressure. The residue was purified on a flash silica gel column (hexanes:EtOAc, 1:1) to give 3 (2.40 g, 82%).

Workup

  1. washthe dichloromethane solution was washed with water (50 mL)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under reduced pressure
  5. customThe residue was purified on a flash silica gel column (hexanes:EtOAc, 1:1)

Sources & evidence

ORD record
ord-0e81b14c40264ccfa4abbea20ac7b045
Source dataset
uspto-grants-2009_09
Patent number
US07582668B2

Linked notes

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