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Methanol → 3-(Phthalimidomethylthio)pyridine

HRID 6127
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 6127
C[N:2]([CH3:12])[C:3]([S:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)=O.[OH-:13].[Na+].C(N([CH2:20][CH3:21])CC)C.[CH3:22][OH:23]>C(O)C>[C:22]1(=[O:23])[N:2]([CH2:3][S:5][C:6]2[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=2)[C:12](=[O:13])[C:6]2=[CH:11][CH:10]=[CH:20][CH:21]=[C:7]12
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 887MethanolHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 299059N,N-dimethyl-1-(pyridin-3-ylsulfanyl)formamide

Produkt 1

HCID 190791383-(Phthalimidomethylthio)pyridineAusbeute 80,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702
Ethanol
Lösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 1.00 g (5.49 mmol) of 3-(dimethylaminocarbonylthio)pyridine in 50 ml of methanol, 5.49 ml (5.49 mmol) of a 1N aqueous solution of sodium hydroxide was added. The mixture was heated at 60° C. for 1 hour with stirring. After cooling, the solvent was distilled off. The residue was dissolved in ethanol and dried. The solvent was distilled off. The residue thus obtained and 1.58 g of (6.59 mmol) of (N-bromomethyl)phthalimide were suspended in 50 ml of ethanol, and 0.92 ml (6.59 mmol) of triethylamine was added. The mixture was stirred at room temperature for 4 hours. The solvent was distilled off, and the residue was dissolved in chloroform, washed with water and dried. Then the solvent was distilled off. The residue was purified by column chromatography (eluent: hexane/ethyl acetate=1:1) to obtain powder. The powder thus obtained was washed with ether and dried to obtain 1.20 g of the desired compound (yield: 80.9%, colorless powder).

Aufarbeitung

  1. temperatureAfter cooling
  2. distillationthe solvent was distilled off
  3. dissolutionThe residue was dissolved in ethanol
  4. customdried
  5. distillationThe solvent was distilled off
  6. customThe residue thus obtained
  7. stirringThe mixture was stirred at room temperature for 4 hours
  8. distillationThe solvent was distilled off
  9. dissolutionthe residue was dissolved in chloroform
  10. washwashed with water
  11. customdried
  12. distillationThen the solvent was distilled off
  13. customThe residue was purified by column chromatography (eluent: hexane/ethyl acetate=1:1)
  14. customto obtain powder
  15. customThe powder thus obtained
  16. washwas washed with ether
  17. customdried

Quellen und Nachweise

ORD-Eintrag
ord-c3e25c8a85d44ea5a75bc8f82e1e111d
Quelldatensatz
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05246948

Notizen zur Reaktion

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