Sulfuryl chloride → 7-(2-(Thieno[3,2-b]pyridin-7-yl)disulfanyl)thieno[3,2-b]pyridine
Reaction equation
[S:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][C:8]=2[SH:10])[CH:3]=[CH:2]1.S(Cl)(Cl)(=O)=O>ClCCl>[S:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][C:8]=2[S:10][S:10][C:8]2[CH:7]=[CH:6][N:5]=[C:4]3[CH:3]=[CH:2][S:1][C:9]=23)[CH:3]=[CH:2]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Thieno[3,2-b]pyridine-7-thiol (1.00 g, 5.9 mmol) was dissolved in dichloromethane (40 mL). The solution was cooled to 0° C. and sulfuryl chloride (1M in dichloromethane, 2.9 mL, 2.9 mmol) was added dropwise and the reaction stirred while warming to ambient temperature. The solution stirred for 5 hours at ambient temperature and then concentrated to dryness. The residue was left standing under open air for two days. The residue was then diluted in dichloromethane and was neutralized with saturation NaHCO3 solution. The organic layer was separated, dried, and concentrated. The residue was triturated with ether and the solid was filtered and dried to provide the title compound (0.37 g, 46% yield) as a tan solid.