Reaction #6201

Reaction equation

4-(3-aminopropylthio)pyridine dihydrochloride

triethylamine

4-anisoyl chloride

→

desired compound

Yield 78.9%

4-[3-(4-methoxybenzoylamino)propylthio]pyridine

Yield 78.9%

Solvents

methylene chloride

Conditions

Workup

1. 1
   Temperaturecooling
2. 2
   workup.STIRRINGthe mixture was stirred for at room temperature for 30 minutes
3. 3
   WashThe reaction mixture was washed with an aqueous saturated sodium bicarbonate solution and water
4. 4
   Otherdried
5. 5
   workup.DISTILLATIONThe solvent was distilled off
6. 6
   OtherThe residue was purified by column chromatography (eluent: ethyl acetate)
7. 7
   Otherto obtain the powder which
8. 8
   Washwas washed with ether
9. 9
   Otherdried

Procedure

To a solution of 1.00 g (4.15 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 2.77 ml (19.8 mmol) of triethylamine in 40 ml of methylene chloride was added 846 mg (4.96 mmol) of 4-anisoyl chloride under ice-cooling with stirring and the mixture was stirred for at room temperature for 30 minutes. The reaction mixture was washed with an aqueous saturated sodium bicarbonate solution and water and dried. The solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate) to obtain the powder which was washed with ether and dried to obtain 990 mg of the desired compound (78.9%, colorless powder), mp: 121.0°-122.0° C.

Source