Benzyl Chloride → HCID 795274, compound

HRID 1059301

Reaction equation

HRID 1059301 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C@H:3]2[CH2:7][CH:8]=[CH:9][CH2:10][C@@H:2]12.C(=O)([O-])[O-].[K+].[K+].[CH2:18](Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C=O.C(OCC)(=O)C>[CH2:18]([N:5]1[C:1](=[O:11])[C@H:2]2[CH2:10][CH:9]=[CH:8][CH2:7][C@H:3]2[C:4]1=[O:6])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 92888cis-1,2,3,6-Tetrahydrophthalimide

Product 1

HCID 795274HCID 795274, compoundYield 81.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

30.2 g of cis-1,2,3,6-tetrahydrophthalimide was dissolved in 200 ml of N,N-dimethylformamide. After adding 38.7 g of potassium carbonate and 30.4 g of benzyl chloride, the resulting mixture was stirred at 50° C. for 3 hours and further at room temperature overnight. Then the reaction mixture was diluted with ethyl acetate and washed with water. The aqueous layer was extracted with ethyl acetate. The organic layer was washed successively with water and a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. After filtering, the solvent was distilled off under reduced pressure. The crude crystals thus obtained were ground and washed with diisopropyl ether and n-hexane followed by filtration. Thus 39.1 g of the title compound was obtained as pale yellow crystals.

Workup

  1. washwashed with water
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washThe organic layer was washed successively with water
  4. dry with materiala saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate
  5. filtrationAfter filtering
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe crude crystals thus obtained
  8. washwashed with diisopropyl ether and n-hexane
  9. filtrationfollowed by filtration

Sources & evidence

ORD record
ord-1c84829974664c1a87c1ce934c36ca5c
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Linked notes

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