Benzoylhydrazine → HCID 58240203, compound

HRID 2176340Notes

Reaction equation

HRID 2176340 reaction equation
C(S[C:4](=[N:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH:5]([CH3:7])[CH3:6])C.[C:15]([NH:23][NH2:24])(=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(O)CCC>[CH:5]([C:4]1[N:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:23][N:24]=1)([CH3:7])[CH3:6]

Participants

4

Reactant 2

HCID 11955BenzoylhydrazineHCID 58068048HCID 58068048, compound

Product 1

HCID 58240203HCID 58240203, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent2×

Conditions

Temperature
130 °C

Procedure

First, 6.1 g of N-[1-(ethylsulfanyl)isobutylidene]aniline, 3.4 g of benzoylhydrazine, and 30 mL of 1-butanol were put in a 200 mL recovery flask, and heated and stirred at 130° C. for 7 hours to be reacted. After the reaction, 1-butanol was distilled off under a reduced pressure to give an oily substance. This oily substance was purified by silica gel column chromatography. As developing solvents, first, dichloromethane was used, and then ethyl acetate was used. The resulting fraction was concentrated to give a white solid. The given solid was recrystallized from a mixed solvent of ethanol and hexane, so that 1.6 g of 3-isopropyl-4,5-diphenyl-4H-1,2,4-triazole was prepared as a white solid with a yield of 24%. The synthetic scheme of Step 1 is shown by (a-8).

Workup

  1. temperatureheated
  2. customto be reacted
  3. distillationwas distilled off under a reduced pressure
  4. customto give an oily substance
  5. customThis oily substance was purified by silica gel column chromatography
  6. concentrationThe resulting fraction was concentrated
  7. customto give a white solid
  8. customThe given solid was recrystallized from a mixed solvent of ethanol and hexane, so that 1.6 g of 3-isopropyl-4,5-diphenyl-4H-1,2,4-triazole
  9. customwas prepared as a white solid with a yield of 24%

Sources & evidence

ORD record
ord-7e297d9f24f64cf1a3eefea1ac11af16
Source dataset
uspto-grants-2015_06
Patent number
US09065061B2

Reaction notes

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