N-(4-Bromobutyl)phthalimide → Phthalimide

HRID 2281971Notes

Reaction equation

HRID 2281971 reaction equation
C[S-].[Na+].BrCCCC[N:9]1[C:13](=[O:14])[C:12]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]2[C:10]1=[O:19]>CO>[C:13]1(=[O:14])[NH:9][C:10](=[O:19])[C:11]2=[CH:18][CH:17]=[CH:16][CH:15]=[C:12]12

Participants

4

Reactant 2

HCID 93575N-(4-Bromobutyl)phthalimideHCID 4378561Sodium methanethiolate

Product 1

HCID 6809PhthalimideYield 149.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

Sodium thiomethoxide (300 mg) was dissolved in methanol (20 ml), N-(4-bromobutyl)phthalimide (1.0 g) was added to the solution, and the resulting mixture was stirred at 65° C. for 18 hours. The reaction mixture was concentrated under reduced pressure, ethyl acetate and distilled water were added to the resulting residue, and the layers were separated. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and filtered, and then the filtrate was concentrated under reduced pressure to obtain a phthalimide compound (778 mg). (2) The compound obtained in (1) mentioned above (775 mg) was dissolved in methylene chloride (23 ml), m-chloroperbenzoic acid (2.06 g) was added to the solution under ice cooling, and the resulting mixture was stirred at room temperature for 17 hours. 10% Aqueous sodium thiosulfate was added to the reaction mixture, the layers were separated, and the organic layer was washed with 10% aqueous sodium thiosulfate, saturated aqueous sodium hydrogencarbonate, distilled water, and saturated aqueous sodium chloride. The organic layer was dried over anhydrous sodium sulfate, and filtered, and then the filtrate was concentrated under reduced pressure to obtain an oxidized compound (854 mg). (3) By using the compound obtained in (2) mentioned above (850 mg) as a starting material, the title compound (256 mg) was obtained in the same manner as that of Reference Example 9, (2).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, ethyl acetate
  2. distillationdistilled water
  3. additionwere added to the resulting residue
  4. customthe layers were separated
  5. washThe organic layer was washed with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c7c4f344064447f39998fe274c3f0cca
Source dataset
uspto-grants-2015_09
Patent number
US09139609B2

Reaction notes

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