Acetic Anhydride → 2-(4-fluorophenyl)-5-methyl-2H-1,2,3-triazol-4-yl acetate

HRID 623694Notes

Reaction equation

HRID 623694 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[N:12]=[C:11]([CH3:13])[CH:10]=[N+:9]2[O-])=[CH:4][CH:3]=1.[C:15]([O:18]C(=O)C)(=[O:17])[CH3:16]>>[C:15]([O:18][C:10]1[C:11]([CH3:13])=[N:12][N:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[N:9]=1)(=[O:17])[CH3:16]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 901115092-(4-fluorophenyl)-4-methyl-2H-1,2,3-triazole 1-oxide2×

Product 1

HCID 901095002-(4-fluorophenyl)-5-methyl-2H-1,2,3-triazol-4-yl acetate

Procedure

2-(4-Fluorophenyl)-4-methyl-2H-1,2,3-triazole 1-oxide (i.e. the product of Step A, 6.6 g, 34 mmol) was added to acetic anhydride (47 mL, 500 mmol), and the reaction mixture was stirred at reflux for 28 h. The reaction was concentrated under reduced pressure. The residue was taken up in ethyl acetate, washed successively with water and saturated aqueous sodium chloride solution, dried with magnesium sulfate and concentrated under reduced pressure to afford the title compound (7.8 g) as a beige solid. The title compound was used directly in the next step without further purification.

Workup

  1. temperatureat reflux for 28 h
  2. concentrationThe reaction was concentrated under reduced pressure
  3. washwashed successively with water and saturated aqueous sodium chloride solution
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b48e8abb97ed4654b32961d88556da64
Source dataset
uspto-grants-2016_04
Patent number
US09302999B2

Reaction notes

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