Reaction #2320151

Reaction equation

N-Formylphenylacetamide

2,3-dichlorophenylhydrazine hydrochloride

→

title compound

5-benzyl-1-(2,3-dichlorophenyl)-1H-1,2,4-triazole

Solvents

acetic acid

Conditions

Workup

1. 1
   Temperaturerefluxed under a nitrogen atmosphere for 1 hour
2. 2
   Concentrationconcentrated under reduced pressure at 60° C
3. 3
   OtherThe residue was purified by flash chromatography
4. 4
   Washeluting with hexanes/ethyl acetate (6/1)

Procedure

N-Formylphenylacetamide (Finkbeiner J. Org. Chem. 1965, 30; 2861) (200 mg, 1.22 mmol) and 2,3-dichlorophenylhydrazine hydrochloride (314 mg, 1.47 mmol) were combined in glacial acetic acid (8 mL) and refluxed under a nitrogen atmosphere for 1 hour and then concentrated under reduced pressure at 60° C. The residue was purified by flash chromatography eluting with hexanes/ethyl acetate (6/1) to provide the title compound. MS (ESI+) m/z 305 (M+1H)+; 1H NMR (300 MHz, DMSO-d6) δ ppm 4.02 (s, 2H) 6.97-7.02 (m, 2H) 7.16-7.25 (m, 3H) 7.52-7.58 (m, 2H) 7.88 (dd, J=6.8, 3.1 Hz, 1H) 8.16 9s, 1 H).

Source