Hydrochloric Acid → HCID 178527726, compound

HRID 1972174Notes

Reaction equation

HRID 1972174 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[CH:9][S:10][C:3]=12.O.O.[SH2:13].[Na].Cl>CCO.O>[S:10]1[C:3]2[C:4](=[N:5][CH:6]=[CH:7][C:2]=2[SH:13])[CH:8]=[CH:9]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 112752517-Chlorothieno[3,2-b]pyridineHCID 86584117Sodium hydrogen sulfide dihydrate2×

Product 1

HCID 178527726HCID 178527726, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

7-chlorothieno[3,2-b]pyridine (1.0 g, 5.9 mmol) in EtOH (15 mL) was treated with sodium hydrogen sulfide dihydrate (3.26 g, 35.4 mmol). The solution was heated at 90° C. overnight. An additional amount of sodium hydrogen sulfide dihydrate (3.26 g, 35.4 mmol) was added and the reaction stirred an additional 20 hours at reflux. The solution was cooled to ambient temperature and diluted with water (100 mL) to dissolve the solids. The solution was cooled to 0° C. and concentrated hydrochloric acid solution was added slowly to adjust the pH to 1. The solution was then filtered and the solid was dried under high vacuum to provide thieno[3,2-b]pyridine-7-thiol (0.73 g, 74% yield) as a yellow solid.

Workup

  1. temperatureat reflux
  2. temperatureThe solution was cooled to ambient temperature
  3. dissolutionto dissolve the solids
  4. temperatureThe solution was cooled to 0° C.
  5. filtrationThe solution was then filtered
  6. customthe solid was dried under high vacuum

Sources & evidence

ORD record
ord-79a77cc711854b9db7d4e130cac6e088
Source dataset
uspto-grants-2013_04
Patent number
US08431713B2

Reaction notes

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