N-Methoxy-N-methylacetamide → 1-(1-(4-vinylphenyl)-1H-1,2,4-triazol-5-yl)ethanone

HRID 587282Notes

Reaction equation

HRID 587282 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:13]=[N:12][CH:11]=[N:10]2)=[CH:5][CH:4]=1)=[CH2:2].[Li]CCCC.CON(C)[C:22](=[O:24])[CH3:23]>C1COCC1>[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([N:9]2[C:13]([C:22](=[O:24])[CH3:23])=[N:12][CH:11]=[N:10]2)=[CH:7][CH:8]=1)=[CH2:2]

Participants

5

Reactant 3

HCID 537505N-Methoxy-N-methylacetamideHCID 585499641-(4-vinylphenyl)-1H-1,2,4-triazoleHCID 178418339Butyllithium

Product 1

HCID 866752191-(1-(4-vinylphenyl)-1H-1,2,4-triazol-5-yl)ethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 1-(4-vinyl-phenyl)-1H-[1,2,4]triazole (1 g, 5.8 mmol) in 25 mL of THF, was added n-BuLi (0.37 g, 5.8 mmol) at −78° C. and stirred for 30 min To this N-methoxy-N-methyl acetamide in THF (0.66 g, 6.4 mmol) was added and the resultant reaction mixture was stirred at ambient temperature for 16 h. The reaction mixture was quenched with a saturated aqueous NH4Cl solution and extracted with EtOAc (3×50 mL). The combined EtOAc layer was washed with brine and dried over sodium sulphate and concentrated under reduced pressure. The crude compound was purified by flash chromatography (SiO2, 100-200 mesh, 40% EtOAc in Pet ether) to afford the title compound as an off white solid (280 mg, 23%): mp 97-98° C.; 1H NMR (400 MHz, CDCl3) δ 8.10 (s, 1H), 7.50 (d, 2H), 7.38 (d, 2H), 6.68 (dd, 1H), 5.85 (d, 1H), 5.38 (d, 1H), 2.75 (s, 3H); ESIMS m/z 214.14 ([M+H]+).

Workup

  1. additionwas added
  2. customthe resultant reaction mixture
  3. customThe reaction mixture was quenched with a saturated aqueous NH4Cl solution
  4. extractionextracted with EtOAc (3×50 mL)
  5. washThe combined EtOAc layer was washed with brine
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customThe crude compound was purified by flash chromatography (SiO2, 100-200 mesh, 40% EtOAc in Pet ether)

Sources & evidence

ORD record
ord-f570ccd375684b3ca262a58444a5e034
Source dataset
uspto-grants-2016_01
Patent number
US09226500B2

Reaction notes

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