Réaction #2487419

Équation de réaction

N-[1-(ethylsulfanyl)ethylidene]aniline

nicotinic acid hydrazide

→

3-Methyl-4-phenyl-5-(3-pyridyl)-4H-1,2,4-triazole

Rendement 42.0%

Solvants

1-butanol

Conditions de réaction

Traitement

1. 1
   AutreFirst, into a 100-mL three-neck flask were placed
2. 2
   ConcentrationAfter the stirring, this reaction solution was concentrated under reduced pressure
3. 3
   Autreto give an oily substance
4. 4
   LavageThis oily substance was washed with ethyl acetate
5. 5
   Filtrationsubjected to suction filtration
6. 6
   Autreto give a solid
7. 7
   AutreThis solid was purified by alumina column chromatography
8. 8
   ConcentrationThe obtained fraction was concentrated
9. 9
   Autreto give a solid
10. 10
    LavageThis solid was washed with a mixed solvent of ethyl acetate and hexane, so that 3-methyl-4-phenyl-5-(3-pyridyl)-4H-1,2,4-triazole (abbreviation: HMpytz)
11. 11
    Autrewas obtained (a white solid, 42% yield)
12. 12
    AutreThe synthesis scheme of Step 1

Mode opératoire

First, into a 100-mL three-neck flask were placed 3.64 g of N-[1-(ethylsulfanyl)ethylidene]aniline, 20 mL of 1-butanol, and 2.78 g of nicotinic acid hydrazide, and the mixture was stirred at 130° C. for 22 hours. After the stirring, this reaction solution was concentrated under reduced pressure to give an oily substance. This oily substance was washed with ethyl acetate, and subjected to suction filtration to give a solid. This solid was purified by alumina column chromatography using ethyl acetate as a developing solvent. The obtained fraction was concentrated to give a solid. This solid was washed with a mixed solvent of ethyl acetate and hexane, so that 3-methyl-4-phenyl-5-(3-pyridyl)-4H-1,2,4-triazole (abbreviation: HMpytz) was obtained (a white solid, 42% yield). The synthesis scheme of Step 1 is illustrated in the following (a-1).

Source