Reaction #2320153

Reaction equation

N-formylphenylacetamide

Phenylhydrazine hydrochloride

triethylamine

→

title compound

5-benzyl-1-phenyl-1H-1,2,4-triazole

Solvents

acetic acid

Conditions

Workup

1. 1
   Temperatureheated at 90° C. for 1 hour
2. 2
   Temperatureto cool to room temperature
3. 3
   Concentrationwas concentrated under reduced pressure
4. 4
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate
5. 5
   Washthe organics were washed with saturated NaHCO3, 1M NaOH, water, and brine
6. 6
   DryingThe organics were then dried (MgSO4)
7. 7
   Filtrationfiltered
8. 8
   Concentrationthe filtrate was concentrated under reduced pressure
9. 9
   OtherThe residue was purified by flash chromatography (40% hexanes/ethyl acetate)

Procedure

Phenylhydrazine hydrochloride (0.09 g, 0.6 mmol) in 5 mL glacial acetic acid was treated with triethylamine (0.06 g, 0.6 mmol), warmed to 70° C., treated with N-formylphenylacetamide (0.1 g, 0.6 mmol), and heated at 90° C. for 1 hour. The mixture was then allowed to cool to room temperature and was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and the organics were washed with saturated NaHCO3, 1M NaOH, water, and brine. The organics were then dried (MgSO4), and filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography (40% hexanes/ethyl acetate) to provide the title compound. MS (ESI) m/e: 236 (M+H)+; 1H NMR (DMSO-d6) δ 4.2 (s, 2H), 7.05-7.1 (d, 2H), 7.17-7.3 (m, 3H), 7.45-7.6 (m, 5H), 8.1 (s, 1H); Anal. calcd. for C, 76.57; H, 5.57; N, 17.86. Found C, 76.32; H: 5.81; N, 17.63.

Source