Hydrochloric Acid → HCID 11040068, compound

HRID 1779952Notes

Reaction equation

HRID 1779952 reaction equation
[Na].[C:2]1([SH:8])C=CC=C[CH:3]=1.[CH2:9](OC(OCC)CBr)[CH3:10].Cl.O1[CH2:23][CH2:22][CH2:21][CH2:20]1>C(O)C.O>[C:20]1([CH2:3][CH:2]=[S:8])[CH:10]=[CH:9][CH:23]=[CH:22][CH:21]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7969ThiophenolHCID 8028TetrahydrofuranHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 5360545Sodium

Product 1

HCID 11040068HCID 11040068, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

23 g (1 mol) of sodium are dissolved in 400 ml of ethanol. After cooling, 110 g (1 mol) of thiophenol are added. 197 g (1 mol) of bromoacetaldehyde diethyl acetal are added dropwise to this mixture. The mixture is heated under reflux for 24 hours and cooled and the salt which has precipitated out is filtered off with suction. The filtrate is concentrated, water is added to the evaporation residue and the mixture is extracted 3 times with ether. The combined ether phases are washed with 1N sodium hydroxide solution and water, dried and concentrated. The evaporation residue obtained is dissolved in 1.2 l of tetrahydrofuran, 1 l of dilute hydrochloric acid is added and the mixture is heated under reflux for 3 hours. It is cooled, diluted with water and extracted 3 times with ether, and the combined ether phases are washed with water, sodium bicarbonate solution and water again, dried and concentrated. 150 g of crude oil are obtained, which is reacted without further purification.

Workup

  1. temperatureAfter cooling
  2. temperatureThe mixture is heated
  3. temperatureunder reflux for 24 hours
  4. temperaturecooled
  5. customthe salt which has precipitated out
  6. filtrationis filtered off with suction
  7. concentrationThe filtrate is concentrated
  8. additionwater is added to the evaporation residue
  9. extractionthe mixture is extracted 3 times with ether
  10. washThe combined ether phases are washed with 1N sodium hydroxide solution and water
  11. customdried
  12. concentrationconcentrated
  13. customThe evaporation residue obtained
  14. temperaturethe mixture is heated
  15. temperatureunder reflux for 3 hours
  16. temperatureIt is cooled
  17. extractionextracted 3 times with ether
  18. washthe combined ether phases are washed with water, sodium bicarbonate solution and water again
  19. customdried
  20. concentrationconcentrated

Sources & evidence

ORD record
ord-4a572968cce84ce8bd26cdac64a2fdee
Source dataset
uspto-grants-1997_05
Patent number
US05629320

Reaction notes

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