Triethylamine → 2-(2-Phthalimidoethylthio)pyridine

HRID 964056Notes

Reaction equation

HRID 964056 reaction equation
C(N(CC)CC)C.[SH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1.Br[CH2:16][CH2:17][N:18]1[C:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]2[C:19]1=[O:28]>C(O)C>[C:19]1(=[O:28])[N:18]([CH2:17][CH2:16][S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[C:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]12

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 178418616HCID 178418616, compound

Product 1

HCID 152314802-(2-Phthalimidoethylthio)pyridineYield 46.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Triethylamine [12.54 ml (90 mmol)] was added to a suspension of 6.67 g (60 mmol) of 2-mercaptopyridine and 15.24 g (60 mmol) of N-(2-bromoethyl)phthalimide in 200 ml of ethanol and stirred at room temperature for 24 hours. The mixture was heated under reflux for 2 hours. The solvent was distilled off, chloroform was added to the residue, and the mixture was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was purified by column chromatography (eluent: ethyl acetate/n-hexane=1:2) to obtain 8.00 g of the desired compound (46.9%, colorless crystals).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. distillationThe solvent was distilled off
  4. additionchloroform was added to the residue
  5. washthe mixture was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off
  8. customthe residue was purified by column chromatography (eluent: ethyl acetate/n-hexane=1:2)

Sources & evidence

ORD record
ord-22919cd1bf444da7b2eb378e59a80a90
Source dataset
uspto-grants-1998_06
Patent number
US05767121

Reaction notes

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