Hydrochloric Acid → Thieno[2,3-c]pyridine-7(6H)-thione

HRID 648541Notes

Reaction equation

HRID 648541 reaction equation
Cl[C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[CH:9][S:8][C:7]=12.O.[SH2:12].[Na].Cl>CN(C)C=O>[S:8]1[C:7]2[C:2](=[S:12])[NH:3][CH:4]=[CH:5][C:6]=2[CH:10]=[CH:9]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 159141297-Chlorothieno[2,3-c]pyridineHCID 53442613Sodium hydrogen sulfide hydrate2×

Product 1

HCID 14666714Thieno[2,3-c]pyridine-7(6H)-thione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(adc) 4.85 g of 7-chloro-thieno[2,3-c]pyridine was dissolved in 15 ml of dimethylformamide and 3.18 g of sodium hydrogen sulfide monohydrate were added under argon. The mixture was heated to 110°-115° for one hour, an additional 1.06 g of sodium hydrogen sulfide monohydrate were added and the mixture was held at the temperature indicated above for an additional hour. The mixture was poured on to 150 ml of ice-water and acidified with 1N aqueous hydrochloric acid solution. After stirring at 2° for a short time, the yellowish crystals were removed by filtration. After recrystallization from a toluene/ethyl acetate mixture, there was obtained pure thieno[2,3-c]pyridine-7(6H)-thione, m.p. 187°-189°.

Workup

  1. temperatureThe mixture was heated to 110°-115° for one hour
  2. customthe yellowish crystals were removed by filtration
  3. customAfter recrystallization from a toluene/ethyl acetate mixture

Sources & evidence

ORD record
ord-e2651c56ad5f4f2daa4e23b56fe14763
Source dataset
uspto-grants-1988_04
Patent number
US04735940

Reaction notes

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