Sodium Hydroxide → 3-Pyridinepropanethiol

HRID 650018Notes

Reaction equation

HRID 650018 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH2:9]Cl)[CH:2]=1.NC(N)=[S:13].[OH-].[Na+]>C(O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH2:9][SH:13])[CH:2]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 2054403-(3-chloropropyl)pyridineHCID 2723790Thiourea

Product 1

HCID 2697793-Pyridinepropanethiol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-(3-pyridyl)-1-propylchloride (3 g; 19.4 mmol) and thiourea (1.48 g; 19.4 mmol) in ethanol (10 mL) was refluxed for 24 hours. Aqueous sodium hydroxide, 15 mL of a 0.75 N solution, was added, and the mixture was refluxed for an additional 2 hours. After cooling to room temperature, the solvent was removed in vacuo. Chromatographic purification of the crude thiol on a silica gel column eluting with 50% ethyl acetate in hexane delivered 1.2 g of 3-(3-Pyridyl)-1-propylmercaptan as a clear liquid. 1H NMR (300 MHz, CDCl3): δ 1.34 (m, 1H); 1.90 (m, 2H); 2.52 (m, 2H); 2.71 (m, 2H); 7.81 (m, 1H); 7.47 (m, 1H) 8.42 (m, 2H).

Workup

  1. temperaturewas refluxed for 24 hours
  2. temperaturethe mixture was refluxed for an additional 2 hours
  3. customthe solvent was removed in vacuo
  4. customChromatographic purification of the crude thiol on a silica gel column
  5. washeluting with 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-578a4b27cd684fd88e3e19df3c89494d
Source dataset
uspto-grants-2001_08
Patent number
US06271244B1

Reaction notes

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