4-(Methylsulfanyl)thiophenol → 3-{[4-(Methylsulfanyl)phenyl]sulfanyl}isonicotinaldehyde

HRID 392285

Reaction equation

HRID 392285 reaction equation
Cl[C:2]1[CH:9]=[N:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:10][S:11][C:12]1[CH:17]=[CH:16][C:15]([SH:18])=[CH:14][CH:13]=1>CN(C=O)C>[CH3:10][S:11][C:12]1[CH:17]=[CH:16][C:15]([S:18][C:2]2[CH:9]=[N:8][CH:7]=[CH:6][C:3]=2[CH:4]=[O:5])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 1368964-(Methylsulfanyl)thiophenolHCID 27629953-Chloro-4-pyridinecarboxaldehyde

Product 1

HCID 226639283-{[4-(Methylsulfanyl)phenyl]sulfanyl}isonicotinaldehydeYield 110.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

3-Chloroisonicotinaldehyde [prepared according to R. B. Moffett et al., J. Heterocycl. Chem. 1979, 16, 1459] (550 mg, 3.9 mmol), 4-methylsulfanyl-benzenethiol (732 mg, 4.7 mmol) potassium carbonate (700 mg, 5.1 mmol) and DMF (10 mL) were combined and the mixture was heated together at 65° C. for 2 h. The solvent was removed in vacuo and the residue was partitioned between EtOAc (50 mL) and water (50 mL). The organic layer was washed with brine, dried (MgSO4) and evaporated to give the title compound (1.124 g) as a yellow oil. The 1H NMR spectrum showed the material to be of sufficient purity (90-95%) to be used without further purification; δH (CDCl3, 300 MHz) 2.52 (3H, s), 7.28 (2H, d), 7.40 (2H, d), 7.64 (1H, d), 8.39 (1H, s), 8.61 (1H, d), 10.42 (1H, s); MS m/z (ES−) 260 (M−H+).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between EtOAc (50 mL) and water (50 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-d290a8cea3ad4fa09adc513686003269
Source dataset
uspto-grants-2004_10
Patent number
US06800652B2

Linked notes

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