Sodium Hydroxide → 3-(4-Phthalimidobutylthio)pyridine

HRID 274629

Reaktionsgleichung

Reaktionsgleichung von HRID 274629
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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 190791033-(4-Phthalimidobutylthio)pyridineAusbeute 4,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-3b4de75034574209ad0146ba4550d376
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05389658

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