1-Chloropentane → HCID 15176722, compound

HRID 1681316Notes

Reaction equation

HRID 1681316 reaction equation
[Na].[CH2:2]([SH:8])[CH2:3][S:4][CH2:5][CH2:6][SH:7].Cl[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]>C(O)C>[CH3:10][CH2:11][CH2:12][CH2:13][CH2:14][S:8][CH2:2][CH2:3][S:4][CH2:5][CH2:6][S:7][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 109771-ChloropentaneHCID 77117Bis(2-mercaptoethyl) sulfideHCID 5360545Sodium

Product 1

HCID 15176722HCID 15176722, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(Compound 1) of formula: ##STR11## 150 ml of absolute ethanol are introduced into a 500 ml three-necked flask, under argon, which is equipped with a thermometer, a condenser and a dropping funnel. Into it are dissolved 4.6 g of sodium (0.20 mole) and heating takes place to 45° C. This is followed by the slow addition of 15.43 g of an ethanolic 3-thia-1,5-pentane dithiol solution (0.10 mole). After stirring for 30 min., slow addition takes place of 25.58 g of an ethanolic 1-chloropentane solution (0.24 mole) and refluxing takes place for 4 hours. The reaction mixture is brought to ambient temperature, followed by filtering. This gives 28.8 g of crude product which is solubilized in 200 ml of dichloromethane and this is all washed with 2×100 ml of distilled water. Drying takes place on MgSO4, followed by filtration. After evaporating the solvent, recrystallization takes place twice in ethanol giving 18.21 g of 6,9,12-trithiaheptadecane, which corresponds to a 62% yield. The said thioether has the following characteristics:

Workup

  1. customwhich is equipped with a thermometer, a condenser and a dropping funnel
  2. temperatureheating
  3. customto 45° C
  4. additionslow addition
  5. temperaturerefluxing
  6. customfor 4 hours
  7. customis brought to ambient temperature
  8. filtrationby filtering
  9. washall washed with 2×100 ml of distilled water
  10. customDrying
  11. filtrationfollowed by filtration
  12. customAfter evaporating
  13. customthe solvent, recrystallization

Sources & evidence

ORD record
ord-ee3cf330921f42249a4e76524a42a805
Source dataset
uspto-grants-1992_12
Patent number
US05171546

Reaction notes

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