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

HRID 1504716Notes

Reaction equation

HRID 1504716 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. customthe resultant reaction mixture
  2. stirringwas stirred at ambient temperature for 16 h
  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-0220dae728d044f9ba31ada2c7b1f9eb
Source dataset
uspto-grants-2015_12
Patent number
US09215870B2

Reaction notes

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