Water → HCID 80640480, compound

HRID 2054156Notes

Reaction equation

HRID 2054156 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[C:11]1[N:16]=[CH:15][C:14]([CH:17]=[O:18])=[CH:13][CH:12]=1.O>CN(C=O)C.CCOC(C)=O>[N:5]1[CH:6]=[CH:7][C:2]([S:1][C:11]2[N:16]=[CH:15][C:14]([CH:17]=[O:18])=[CH:13][CH:12]=2)=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 117692346-Bromo-3-pyridinecarboxaldehydeHCID 178418431pyridine-4-thiol

Product 1

HCID 80640480HCID 80640480, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-mercaptopyridine (5.59 g, 50.3 mmol) in DMF (100 mL) was added NaH (60% dispersion in oil, 1.99 g, 49.7 mmol) in portions and the mixture was stirred for 20 min. 6-Bromo-3-pyridine carboxaldehyde (9.22 g, 49.6 mmol) was added and the resultant mixture was stirred for 1 h. Water was added followed by the addition of EtOAc. The phases were separated and the aqueous layer was extracted with EtOAc (2×). The organic extracts were combined, dried over Na2SO4, filtered and concentrated in vacuo to give a crude product, which was purified by recrystallization from EtOAc. The resultant colored solid was filtered through a silica gel column (eluent: MTBE). Evaporation of the filtrate and further recrystallization from MTBE gave the product as a white solid (8.1 g, 76% yield).

Workup

  1. customThe phases were separated
  2. extractionthe aqueous layer was extracted with EtOAc (2×)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a crude product, which
  7. customwas purified by recrystallization from EtOAc
  8. filtrationThe resultant colored solid was filtered through a silica gel column (eluent: MTBE)
  9. customEvaporation of the filtrate and further recrystallization from MTBE

Sources & evidence

ORD record
ord-dc20848ac6404756af820deecca13f27
Source dataset
uspto-grants-2008_02
Patent number
US07329656B2

Reaction notes

Loading…