Triethylamine → 4-(3-Hydroxypropylthio)pyridine

HRID 6131

Reaction equation

HRID 6131 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Br[CH2:16][CH2:17][CH2:18][OH:19]>C(Cl)Cl>[OH:19][CH2:18][CH2:17][CH2:16][S:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 123083-Bromo-1-propanolHCID 178418431pyridine-4-thiol

Product 1

HCID 190791344-(3-Hydroxypropylthio)pyridineYield 62.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 250 ml of methylene chloride was dissolved 22.2 g (200 mmol) of 4-mercaptopyridine and 27.9 ml (200 mmol) of triethylamine. Thereto was added 18.1 g (200 mmol) of 3-bromo-1-propanol. The mixture was stirred at room temperature for 3 hours. The reaction mixture was washed with a 1N aqueous solution of sodium hydroxide and water and dried. Then the solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate) to obtain 21.3 g of the desired compound (yield: 62.9%, yellow oil).

Workup

  1. washThe reaction mixture was washed with a 1N aqueous solution of sodium hydroxide and water
  2. customdried
  3. distillationThen the solvent was distilled off
  4. customThe residue was purified by column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-78e604ab97a5457d90db9847ffc8eaa3
Source dataset
uspto-grants-1993_09
Patent number
US05246948

Linked notes

Loading…