Triethylamine → 2-[3-(4-chlorophenyl)propyl]-1H-isoindole-1,3(2H)-dione

HRID 1766013

Reaction equation

HRID 1766013 reaction equation
S(Cl)(C)(=O)=O.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15]O)=[CH:9][CH:8]=1.C(N(CC)CC)C.[C:24]1(=[O:34])[NH:28][C:27](=[O:29])[C:26]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:25]12.[K].[OH-].[Na+]>O1CCCC1.CN(C)C=O.O>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][CH2:14][CH2:15][N:28]2[C:24](=[O:34])[C:25]3[C:26](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:27]2=[O:29])=[CH:11][CH:12]=1

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 2219714-ChlorobenzenepropanolHCID 24194345Phthalimide potassium salt

Product 1

HCID 178489072-[3-(4-chlorophenyl)propyl]-1H-isoindole-1,3(2H)-dioneYield 92.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Mesyl chloride (2.10 ml, 27.1 mmol) was added to a solution of 3-(4-chlorophenyl)propyl alcohol (4.6 g, 27 mmol) obtained in 1) above and triethylamine (3.78 ml, 27.1 mmol) in tetrahydrofuran (100 ml) at 0° C. and stirred at room temperature for 30 minutes. Water was added to the reaction mixture which was then extracted with ethyl acetate. The extract was washed with an aqueous saturated NaCl solution and dried over anhydrous magnesium sulfate. After the solvent was distilled away under reduced pressure, the reaction mixture and potassium phthalimide (5.02 g, 27.1 mmol) were dissolved in dimethylformamide and heated at 80° C. for 10 hours under stirring. 8 N aqueous sodium hydroxide was added to the resultant solution which was then extracted with ethyl acetate. The extract was washed with an aqueous saturated NaCl solution and dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure, whereby 7.47 g 2-[3-(4-chlorophenyl)propyl]-1H-isoindole-1,3(2H)-dione was obtained as solid.

Workup

  1. extractionwas then extracted with ethyl acetate
  2. washThe extract was washed with an aqueous saturated NaCl solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationAfter the solvent was distilled away under reduced pressure
  5. temperatureheated at 80° C. for 10 hours
  6. stirringunder stirring
  7. extractionwas then extracted with ethyl acetate
  8. washThe extract was washed with an aqueous saturated NaCl solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. distillationThe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-ad7a9c8a03a7489e8fad45aebf568bb8
Source dataset
uspto-grants-2007_06
Patent number
US07229986B2

Linked notes

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