Reaktion #6220

Reaktionsgleichung

4-(3-aminopropylthio)pyridine

5-methyl-2-thiophenecarboxylic acid

N-hydroxysuccinimide

1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride

→

desired compound

Ausbeute 64.5%

4-[3-(5-methylthenoylamino)propylthio]pyridine

Ausbeute 64.5%

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooling
2. 2
   workup.STIRRINGThe mixture was stirred at room temperature for 1 hour
3. 3
   workup.STIRRINGthe mixture was stirred at room temperature for 2 hours
4. 4
   WaschenThe reaction mixture was washed with water
5. 5
   Sonstigedried
6. 6
   workup.DISTILLATIONthe solvent was distilled off
7. 7
   SonstigeThe residue was purified by column chromatography (eluent: ethyl acetate)
8. 8
   Sonstigeto obtain powder
9. 9
   SonstigeThe powder thus obtained
10. 10
    Waschenwas washed with ether
11. 11
    Sonstigedried

Vorschrift

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 1-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).

Quelle