Pyridine → N-{4-[(3-Chloropropyl)sulfanyl]phenyl}acetamide

HRID 127930Notes

Reaction equation

HRID 127930 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][CH2:12][CH2:13][CH2:14]O)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].N1C=CC=CC=1.S(Cl)([Cl:24])=O>C(Cl)Cl>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][CH2:12][CH2:13][CH2:14][Cl:24])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 23470789HCID 23470789, compound

Product 1

HCID 14005891N-{4-[(3-Chloropropyl)sulfanyl]phenyl}acetamideYield 57.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred suspension of 5.62 g (0.025 mole) of 3-(4'-acetamidophenylthio)propanol in 25 ml of methylene chloride and 2.03 ml of pyridine (0.025 mole) is added 3.7 g of thionyl chloride (0.031 mole) in 10 ml of methylene chloride. After the exothermic reaction subsides, the mixture is heated at reflux for 0.5 hr. The reaction mixture is poured into 100 ml of ice-water with stirring. The organic layer is separated, dried and concentrated to a dark red solid. Extraction of the latter with ether in a Soxlet apparatus yields 3.5 g of 3-(p-acetamidophenylthio)propyl chloride having the correct IR and NMR spectra.

Workup

  1. customAfter the exothermic reaction subsides
  2. temperaturethe mixture is heated
  3. temperatureat reflux for 0.5 hr
  4. customThe organic layer is separated
  5. customdried
  6. concentrationconcentrated to a dark red solid
  7. extractionExtraction of the latter with ether in a Soxlet apparatus

Sources & evidence

ORD record
ord-24d1c014e33942fbb9b03058e30bb6e4
Source dataset
uspto-grants-1981_03
Patent number
US04258045

Reaction notes

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