5-Methylthiophene-2-carboxylic acid → 4-[3-(5-Methylthenoylamino)propylthio]pyridine

To a solution of 1.27 g (8.91 mmol) of 5-methyl-2-thiophenecarboxylic acid and 1.33 g (11.6 mmol) of N-hydroxysuccinimide in 90 ml of methylene chloride, 2.05 g (10.7 mmol) of t-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added under ice-cooling with stirring. The mixture was stirred at room temperature for 1 hour. Further, 1.50 g (8.91 mmol) of 4-(3-aminopropylthio)pyridine was added, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was washed with water and dried, and then the solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate) to obtain powder. The powder thus obtained was washed with ether and dried to obtain 1.68 g of the desired compound (yield: 64.5%, colorless powder).

1. temperaturecooling
2. stirringThe mixture was stirred at room temperature for 1 hour
3. stirringthe mixture was stirred at room temperature for 2 hours
4. washThe reaction mixture was washed with water
5. customdried
6. distillationthe solvent was distilled off
7. customThe residue was purified by column chromatography (eluent: ethyl acetate)
8. customto obtain powder
9. customThe powder thus obtained
10. washwas washed with ether
11. customdried

ORD-Eintrag

ord-1d2aa6f338be4994ac048c0e4b102156

Quelldatensatz

uspto-grants-1996_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05561147