Methanol → 3-(Phthalimidomethylthio)pyridine

Temperature

60 °C

To a solution of 1.00 g (5.49 mmol) of 3-(dimethylaminocarbonylthio)pyridine in 50 ml of methanol, 5.49 ml (5.49 mmol) of a 1N aqueous solution of sodium hydroxide was added. The mixture was heated at 60° C. for 1 hour with stirring. After cooling, the solvent was distilled off. The residue was dissolved in ethanol and dried. The solvent was distilled off. The residue thus obtained and 1.58 g of (6.59 mmol) of (N-bromomethyl)phthalimide were suspended in 50 ml of ethanol, and 0.92 ml (6.59 mmol) of triethylamine was added. The mixture was stirred at room temperature for 4 hours. The solvent was distilled off, and the residue was dissolved in chloroform, washed with water and dried. Then the solvent was distilled off. The residue was purified by column chromatography (eluent: hexane/ethyl acetate=1:1) to obtain powder. The powder thus obtained was washed with ether and dried to obtain 1.20 g of the desired compound (yield: 80.9%, colorless powder).

1. temperatureAfter cooling
2. distillationthe solvent was distilled off
3. dissolutionThe residue was dissolved in ethanol
4. customdried
5. distillationThe solvent was distilled off
6. customThe residue thus obtained
7. stirringThe mixture was stirred at room temperature for 4 hours
8. distillationThe solvent was distilled off
9. dissolutionthe residue was dissolved in chloroform
10. washwashed with water
11. customdried
12. distillationThen the solvent was distilled off
13. customThe residue was purified by column chromatography (eluent: hexane/ethyl acetate=1:1)
14. customto obtain powder
15. customThe powder thus obtained
16. washwas washed with ether
17. customdried

ORD record

ord-c3e25c8a85d44ea5a75bc8f82e1e111d

Source dataset

uspto-grants-1993_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05246948