Triethylamine → 4-(3-Hydroxypropylthio)pyridine

HRID 6119

Reaction equation

HRID 6119 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 83.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 100 ml of methylene chloride were dissolved 11.1 g (100 mmol) of 4-mercaptopyridine and 13.9 ml (100 mmol) of triethylamine, and 9.04 ml (100 mmol) of 3-bromo-1-propanol was added. The mixture was stirred at room temperature for 2 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 14.2 g of the desired compound (yield: 83.9%, yellow oil).

Workup

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

Sources & evidence

ORD record
ord-e97eadac01b44ac8865f4b6513251185
Source dataset
uspto-grants-1993_09
Patent number
US05246948

Linked notes

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