Phenylhydrazine → 1,3-Diphenyl-1H-1,2,4-triazole-5-methanol

HRID 1621150Notes

Reaction equation

HRID 1621150 reaction equation
[C:1]1([C:7]2[O:8][CH2:9][C:10](=O)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:13]1([NH:19][NH2:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(O)C>[C:13]1([N:19]2[C:10]([CH2:9][OH:8])=[N:11][C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[N:20]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 69174032-Phenyloxazol-4(5H)-one

Product 1

HCID 132241301,3-Diphenyl-1H-1,2,4-triazole-5-methanolYield 60.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-phenyloxazol-4(5H)-one (600 mg, 3.35 mmol) and phenylhydrazine (420 mg, 382 μL, 3.69 mmol) in ethanol (10 mL) was refluxed for 2 h. The reaction mixture was concentrated in vacuo. The obtained suspension was filtered, washed with EtOH and dried in vacuo to give 513 mg of a light yellow solid which proofed to be product. The filtrate was evaporated to give 430 mg of a yellow solid which also contained a considerable amount of product. Thus, the product was obtained after purification of the evaporated filtrate by flash chromatography (using silica gel and an ethyl acetate/dichloromethane gradient) and combination with the precipitated product as light yellow solid (711 mg, 2.83 mmol, 84.4%). MS: M=252.2 (M+H)+

Workup

  1. temperaturewas refluxed for 2 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. filtrationThe obtained suspension was filtered
  4. washwashed with EtOH
  5. customdried in vacuo

Sources & evidence

ORD record
ord-bb17ebfac2694cbeb9a25ab27e647ee5
Source dataset
uspto-grants-2014_07
Patent number
US08772510B2

Reaction notes

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