Benzophenone → Benzimidazole

HRID 1436163Notes

Reaction equation

HRID 1436163 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.[CH2:24](Cl)Cl>>[N:9]1[C:8]2[CH:18]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][CH:24]=1

Participants

4

Reactant 3

HCID 3102BenzophenoneHCID 6344DichloromethaneHCID 196971Aminoacetonitrile sulfate (1:1)

Product 1

HCID 5798BenzimidazoleYield 82%

Procedure

To a stirred solution of 2-aminoacetonitrile bisulfate (2.9 g, 0.013 mmol) in DCM (50 mL) was added benzophenone (3.48 mL, 0.0208 mmol) followed by DEIA (4.53 mL, 0.026 mmol). After stirring 18 h, the DCM 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 DCM 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-215061ab33f445949c0e2e115b9c5b8e
Source dataset
uspto-grants-2009_11
Patent number
US07618981B2

Reaction notes

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