N-(Hydroxymethyl)nicotinamide → 4-(3-Picolinoylaminomethylthio)pyridine

HRID 864005Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 864005
[SH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.O[CH2:9][NH:10][C:11](=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[N:14][CH:13]=1>FC(F)(F)C(O)=O>[N:14]1[CH:15]=[CH:16][CH:17]=[C:12]([C:11]([NH:10][CH2:9][S:1][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=2)=[O:18])[CH:13]=1

Komponenten

4

Edukt 2

HCID 77116N-(Hydroxymethyl)nicotinamideHCID 178418431pyridine-4-thiol

Produkt 1

HCID 539677474-(3-Picolinoylaminomethylthio)pyridineAusbeute 15,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

To a mixture of 1.11 g (10 mmol) of 4-mercaptopyridine and 1.52 g (10 mmol) of N-(hydroxymethyl)nicotinamide, 30 ml of trifluoroacetic acid was added, and the mixture was stirred at room temperature for 1 hour. The solvent was distilled off and 30 ml of ethanol was added to the residue. The solvent was distilled off and water was added to the residue. The mixture was neutralized with saturated aqueous sodium bicarbonate, followed by extraction with chloroform. After washing with saturated saline, the extract was dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was purified by column chromatography (eluent:ethyl acetate/ethanol=5:1) to give 390 mg of the desired compound (15.9% yield, yellow solid).

Aufarbeitung

  1. additionwas added
  2. distillationThe solvent was distilled off
  3. addition30 ml of ethanol was added to the residue
  4. distillationThe solvent was distilled off
  5. additionwater was added to the residue
  6. extractionfollowed by extraction with chloroform
  7. washAfter washing with saturated saline
  8. dry with materialthe extract was dried over anhydrous magnesium sulfate
  9. distillationThe solvent was distilled off
  10. customthe residue was purified by column chromatography (eluent:ethyl acetate/ethanol=5:1)

Quellen und Nachweise

ORD-Eintrag
ord-c78edb6d106e48d2801abaea7c5e3db0
Quelldatensatz
uspto-grants-1996_10
Patentnummer
US05561147

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