Reaction #2487419

Reaction equation

N-[1-(ethylsulfanyl)ethylidene]aniline

nicotinic acid hydrazide

→

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

Yield 42.0%

Solvents

1-butanol

Conditions

Workup

1. 1
   OtherFirst, into a 100-mL three-neck flask were placed
2. 2
   ConcentrationAfter the stirring, this reaction solution was concentrated under reduced pressure
3. 3
   Otherto give an oily substance
4. 4
   WashThis oily substance was washed with ethyl acetate
5. 5
   Filtrationsubjected to suction filtration
6. 6
   Otherto give a solid
7. 7
   OtherThis solid was purified by alumina column chromatography
8. 8
   ConcentrationThe obtained fraction was concentrated
9. 9
   Otherto give a solid
10. 10
    WashThis 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
    Otherwas obtained (a white solid, 42% yield)
12. 12
    OtherThe synthesis scheme of Step 1

Procedure

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