Nicotinic acid, hydrazide → HCID 58068033, compound

HRID 2400237Notes

Reaction equation

HRID 2400237 reaction equation
C(S[C:4](=[N:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:5])C.[C:13]([NH:21][NH2:22])(=O)[C:14]1[CH:19]=[CH:18][CH:17]=[N:16][CH:15]=1>C(O)CCC>[CH3:5][C:4]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:13]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)=[N:21][N:22]=1

Participants

4

Reactant 2

HCID 11112Nicotinic acid, hydrazideHCID 13115188HCID 13115188, compound

Product 1

HCID 58068033HCID 58068033, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

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).

Workup

  1. customFirst, into a 100-mL three-neck flask were placed
  2. concentrationAfter the stirring, this reaction solution was concentrated under reduced pressure
  3. customto give an oily substance
  4. washThis oily substance was washed with ethyl acetate
  5. filtrationsubjected to suction filtration
  6. customto give a solid
  7. customThis solid was purified by alumina column chromatography
  8. concentrationThe obtained fraction was concentrated
  9. customto give a solid
  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. customwas obtained (a white solid, 42% yield)
  12. customThe synthesis scheme of Step 1

Sources & evidence

ORD record
ord-5836501a40be48339f27df694a96bcd8
Source dataset
uspto-grants-2014_08
Patent number
US08795851B2

Reaction notes

Loading…