Sulfuryl chloride → 7-(2-(Thieno[3,2-b]pyridin-7-yl)disulfanyl)thieno[3,2-b]pyridine

HRID 1972175Notes

Reaction equation

HRID 1972175 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]1

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 178527726HCID 178527726, compound

Product 1

HCID 866409897-(2-(Thieno[3,2-b]pyridin-7-yl)disulfanyl)thieno[3,2-b]pyridineYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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.

Workup

  1. temperaturewhile warming to ambient temperature
  2. stirringThe solution stirred for 5 hours at ambient temperature
  3. concentrationconcentrated to dryness
  4. waitThe residue was left
  5. additionThe residue was then diluted in dichloromethane
  6. customThe organic layer was separated
  7. customdried
  8. concentrationconcentrated
  9. customThe residue was triturated with ether
  10. filtrationthe solid was filtered
  11. customdried

Sources & evidence

ORD record
ord-f56912a7db344e028515a47d106c52ac
Source dataset
uspto-grants-2013_04
Patent number
US08431713B2

Reaction notes

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