Benzoylhydrazine → HCID 68380230, compound

HRID 1748963Notes

Reaction equation

HRID 1748963 reaction equation
[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][C:2]=1[NH:14][C:15](=S)[CH:16]([CH3:18])[CH3:17].[C:20]([NH:28][NH2:29])(=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(O)CCC>[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][C:2]=1[N:14]1[C:15]([CH:16]([CH3:18])[CH3:17])=[N:29][N:28]=[C:20]1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 11955BenzoylhydrazineHCID 86671704HCID 86671704, compound

Product 1

HCID 68380230HCID 68380230, compoundYield 7.4%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
130 °C

Procedure

In a 200 mL three-neck flask were put 13 g (50 mmol) of N-(9H-fluoren-2-yl)isobutyrthioamide, 8.2 g (60 mmol) of benzoylhydrazine, and 70 mL of 1-butanol, and the mixture was heated and refluxed at 130° C. for 10 hours. After that, the solid in the reaction mixture was removed by suction filtration. The resulting filtrate was concentrated to precipitate a solid. After that, 1-buthanol was distilled off to precipitate a solid. The precipitated solid was removed by suction filtration, and the filtrate was purified by silica gel column chromatography. A mixed solvent of ethyl acetate and toluene (ethyl acetate: toluene=1:1) was used as a developing solvent. The resulting fraction was concentrated to give a solid. The obtained solid was recrystallized from ethyl acetate to give 1.3 g of a white solid of 4-(9H-fluoren-2-yl)-5-isopropyl-3-phenyl-4H-1,2,4-triazole in a yield of 7%. The synthesis scheme of Step 3 is shown in (c-3) below.

Workup

  1. customIn a 200 mL three-neck flask were put
  2. customAfter that, the solid in the reaction mixture was removed by suction filtration
  3. concentrationThe resulting filtrate was concentrated
  4. customto precipitate a solid
  5. distillationAfter that, 1-buthanol was distilled off
  6. customto precipitate a solid
  7. customThe precipitated solid was removed by suction filtration
  8. customthe filtrate was purified by silica gel column chromatography
  9. concentrationThe resulting fraction was concentrated
  10. customto give a solid
  11. customThe obtained solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-4f735dd5c5944aed9a17e629b8789f79
Source dataset
uspto-grants-2015_10
Patent number
US09155158B2

Reaction notes

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