Benzamidine → HCID 22563291, compound

HRID 1716555Notes

Reaction equation

HRID 1716555 reaction equation
Br[CH:2]([C:16](=O)[CH3:17])[CH2:3][CH2:4][N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15].[C:19]([NH2:27])(=[NH:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:17][C:16]1[NH:27][C:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:26][C:2]=1[CH2:3][CH2:4][N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15]

Participants

5

Reactant 3

HCID 2332BenzamidineHCID 11430Potassium CarbonateHCID 15670030HCID 15670030, compound

Product 1

HCID 22563291HCID 22563291, compoundYield 41.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-(3-bromo-4-oxo-pentyl)-isoindole-1,3-dione (12.4 g) [CAS 112357-34-3] in abs. DMF (50 ml) was added benzamidine 85% (5.65 g) and potassium carbonate (11.03 g). The reaction mixture was stirred at 80° C. for 4 h, concentrated under vacuum. To the residue was added ice/water, and the mixture was extracted with ethyl acetate. The organic phase washed with water and brine, dried over magnesium sulphate and concentrated. The crude product was purified by chromatography on silica gel using methylene chloride/methanol 5% and 10% as eluent to obtain 2-[2-(5-methyl-2-phenyl-1H-imidazol-4-yl)-ethyl]-isoindole-1,3-dione (5.5 g) as a yellow foam.

Workup

  1. concentrationconcentrated under vacuum
  2. additionTo the residue was added ice/water
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic phase washed with water and brine
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated
  7. customThe crude product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-c94e81a31cf6452581b23783b6c9130f
Source dataset
uspto-grants-2010_09
Patent number
US07803819B2

Reaction notes

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