Chlorosuccinimide → 1-Allyl-4-chloro-7-(1-ethylpropyl)-1,3-dihydro-2H-benzimidazol-2-one

HRID 1628458Notes

Reaction equation

HRID 1628458 reaction equation
[CH2:1]([N:4]1[C:8]2[C:9]([CH:13]([CH2:16][CH3:17])[CH2:14][CH3:15])=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][C:5]1=[O:18])[CH:2]=[CH2:3].[Cl:19]N1C(=O)CCC1=O>C1(C)C=CC=CC=1.[Cl-].[Zr+4].[Cl-].[Cl-].[Cl-]>[CH2:1]([N:4]1[C:8]2[C:9]([CH:13]([CH2:16][CH3:17])[CH2:14][CH3:15])=[CH:10][CH:11]=[C:12]([Cl:19])[C:7]=2[NH:6][C:5]1=[O:18])[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 687707121-Allyl-7-(1-ethylpropyl)-1,3-dihydro-2H-benzimidazol-2-one

Product 1

HCID 687711291-Allyl-4-chloro-7-(1-ethylpropyl)-1,3-dihydro-2H-benzimidazol-2-oneYield 38.3%

Reagents, catalysts & solvents 2

HCID 9856075Zirconium chloride (ZrCl4), (T-4)-CatalystHCID 1140TolueneSolvent

Procedure

To a mixture of 1-allyl-7-(1-ethylpropyl)-1,3-dihydro-2H-benzimidazol-2-one (22.0 g, 89.8 mmol) and zirconium chloride (1.05 g, 4.49 mmol) in toluene (300 mL) was added N-chlorosuccinimide (12.4 g, 92.5 g) portionwise at 0° C. After stirring for 15 hr, the mixture was concentrated in vacuo to give a residue which was partitioned in aqueous sodium bicarbonate and ethyl acetate. The aqueous layer was extracted with ethyl acetate. Combined organic layer was washed with aqueous sodium bicarbonate and brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was dissolved in hot ethyl acetate. n-Hexane was then added and the solution was cooled down. Resulting precipitate was collected by filtration to afford the title compound (9.60 g, 34.4 mmol, 38%) as a colorless solid.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customto give a residue which
  3. customwas partitioned in aqueous sodium bicarbonate
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washCombined organic layer was washed with aqueous sodium bicarbonate and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. dissolutionThe residue was dissolved in hot ethyl acetate
  9. additionn-Hexane was then added
  10. temperaturethe solution was cooled down
  11. customResulting precipitate
  12. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-b8287fe0c01340a5b41a531eb81bd547
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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