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

HRID 6166Notes

Reaction equation

HRID 6166 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 539677474-(3-Picolinoylaminomethylthio)pyridineYield 15.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-eac925e9b2f940fdb1f04bc16132b520
Source dataset
uspto-grants-1993_09
Patent number
US05246948

Reaction notes

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