Water → Phthalimide

HRID 2281962Notes

Reaction equation

HRID 2281962 reaction equation
BrCCCC[N:6]1[C:10](=[O:11])[C:9]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:8]2[C:7]1=[O:16].O>CN(C)C=O>[C:10]1(=[O:11])[NH:6][C:7](=[O:16])[C:8]2=[CH:15][CH:14]=[CH:13][CH:12]=[C:9]12

Participants

4

Reactant 2

HCID 962WaterHCID 93575N-(4-Bromobutyl)phthalimide

Product 1

HCID 6809PhthalimideYield 103.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

70% Sodium hydride (827 mg) was suspended in dimethylformamide (20 ml), a solution of 4-(3-pyridinyl)-1H-imidazole (3.0 g) obtained by the method described in the publication (International Patent Publication WO00/02875) in dimethylformamide (10 ml) was added to the suspension under ice cooling, and the resulting mixture was stirred at the same temperature for 5 minutes. A solution of N-(4-bromobutyl)phthalimide (5.84 g) in dimethylformamide (10 ml) was added to the reaction mixture, and the resulting mixture was stirred at 60° C. for 4 hours. Distilled water was added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with aqueous sodium hydrogencarbonate, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, the resulting residue was dissolved in ethyl acetate, and hexane was added to the solution to deposit a solid. The deposited solid was collected by filtration to obtain a phthalimide compound (3.16 g). (2) By using the compound obtained in (1) mentioned above (3.16 g) as a starting material, the title compound (1.94 g) was obtained in the same manner as that of Reference Example 9, (2).

Workup

  1. additionwas added to the suspension under ice cooling
  2. stirringthe resulting mixture was stirred at 60° C. for 4 hours
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with aqueous sodium hydrogencarbonate
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. dissolutionthe resulting residue was dissolved in ethyl acetate
  9. additionhexane was added to the solution
  10. filtrationThe deposited solid was collected by filtration

Sources & evidence

ORD record
ord-457a6925c7194b0c88b9ed298915a655
Source dataset
uspto-grants-2015_09
Patent number
US09139609B2

Reaction notes

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