N-formyl-2-phenylacetamide → 5-benzyl-1-(2,3-dichlorophenyl)-1H-1,2,4-triazole

HRID 2232969Notes

Reaction equation

HRID 2232969 reaction equation
[CH:1]([NH:3][C:4](=O)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.Cl.[Cl:14][C:15]1[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=1[NH:22][NH2:23]>C(O)(=O)C>[CH2:5]([C:4]1[N:22]([C:16]2[CH:17]=[CH:18][CH:19]=[C:20]([Cl:21])[C:15]=2[Cl:14])[N:23]=[CH:1][N:3]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 3268658N-formyl-2-phenylacetamideHCID 122765722,3-Dichlorophenylhydrazine HCl

Product 1

HCID 166789045-benzyl-1-(2,3-dichlorophenyl)-1H-1,2,4-triazole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

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).

Workup

  1. temperaturerefluxed under a nitrogen atmosphere for 1 hour
  2. concentrationconcentrated under reduced pressure at 60° C
  3. customThe residue was purified by flash chromatography
  4. washeluting with hexanes/ethyl acetate (6/1)

Sources & evidence

ORD record
ord-59258f021c294dd98808f01ec494dca2
Source dataset
uspto-grants-2010_05
Patent number
US07709469B2

Reaction notes

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