Sodium Hydroxide → 3-(4-Phthalimidobutylthio)pyridine

HRID 274629

Reaction equation

HRID 274629 reaction equation
CN(N[C:5]([S:7][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)=O)C.[OH-].[Na+].BrC[CH2:18][CH2:19][CH2:20][N:21]1[C:25](=[O:26])[C:24]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]2[C:22]1=[O:31]>CO>[C:22]1(=[O:31])[N:21]([CH2:20][CH2:19][CH2:18][CH2:5][S:7][C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[C:25](=[O:26])[C:24]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]12

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 93575N-(4-Bromobutyl)phthalimideHCID 190790823-Dimethylaminocarbamoylthiopyridine

Product 1

HCID 190791033-(4-Phthalimidobutylthio)pyridineYield 4.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3.64 g (20 mmol) of 3-dimethylaminocarbamoylthiopyridine in 100 ml of methanol was added 1.6 g (40 mmol) of sodium hydroxide. The mixture was heated and refluxed for 3 hours under nitrogen atmosphere. After cooling, 5.64 g (20 mmol) of N-(4-bromobutyl)phthalimide was added. The mixture was heated and refluxed for 2.5 hours. The solvent was distilled off and chloroform was added to the residue. The mixture was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was purified by column chromatography (eluent: ethyl acetate/n-hexane=1:1) to obtain 280 mg of the desired compound (4.5%, colorless oil).

Workup

  1. temperatureThe mixture was heated
  2. temperaturerefluxed for 3 hours under nitrogen atmosphere
  3. temperatureAfter cooling
  4. temperatureThe mixture was heated
  5. temperaturerefluxed for 2.5 hours
  6. distillationThe solvent was distilled off
  7. additionchloroform was added to the residue
  8. washThe mixture was washed with water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. distillationThe solvent was distilled off
  11. customthe residue was purified by column chromatography (eluent: ethyl acetate/n-hexane=1:1)

Sources & evidence

ORD record
ord-3b4de75034574209ad0146ba4550d376
Source dataset
uspto-grants-1995_02
Patent number
US05389658

Linked notes

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