Benzoylhydrazine → HCID 58240228, compound

HRID 2176339Notes

Reaction equation

HRID 2176339 reaction equation
C(S[C:4](=[N:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:5][CH2:6][CH3:7])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>[C:16]1([C:15]2[N:8]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:4]([CH2:5][CH2:6][CH3:7])=[N:24][N:23]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 11955BenzoylhydrazineHCID 26295819255-90-4

Product 1

HCID 58240228HCID 58240228, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
130 °C

Procedure

Next, 5.40 g of N-[1-(ethylsulfanyl)butylidene]aniline, 3.19 g of benzoylhydrazine, and 30 mL of 1-butanol were put in a 100 mL three-neck flask and heated and stirred at 130° C. for 12 hours. After the stirring, butanol was distilled off under a reduced pressure to give a brown solid. This solid was washed with ethyl acetate, and subjected to suction filtration to give a solid. The given solid was purified by silica gel column chromatography. As developing solvents, first, hexane:ethyl acetate=1:9 was used, and then ethyl acetate was used. The resulting fraction was concentrated to give a solid. This solid was recrystallized from a mixed solvent of hexane and ethyl acetate, so that 3,4-diphenyl-5-propyl-4H-1,2,4-triazole (abbreviation: HPrptz) was prepared (a white solid, yield: 28%). The synthetic scheme of Step 4 is shown by (d-7).

Workup

  1. temperatureheated
  2. distillationAfter the stirring, butanol was distilled off under a reduced pressure
  3. customto give a brown solid
  4. washThis solid was washed with ethyl acetate
  5. filtrationsubjected to suction filtration
  6. customto give a solid
  7. customThe given solid was purified by silica gel column chromatography
  8. concentrationThe resulting fraction was concentrated
  9. customto give a solid
  10. customThis solid was recrystallized from a mixed solvent of hexane and ethyl acetate, so that 3,4-diphenyl-5-propyl-4H-1,2,4-triazole (abbreviation: HPrptz)
  11. customwas prepared (a white solid, yield: 28%)

Sources & evidence

ORD record
ord-5e1ac19467cd4948b8317108262d67c4
Source dataset
uspto-grants-2015_06
Patent number
US09065061B2

Reaction notes

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