Acetic Anhydride → 1-(4-Iodo-3,5-dimethyl-1H-pyrazol-1-yl)ethanone

HRID 1453012

Reaction equation

HRID 1453012 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.C(N(CC)CC)C.[CH3:15][C:16]1[C:20]([I:21])=[C:19]([CH3:22])[NH:18][N:17]=1>C(Cl)Cl>[I:21][C:20]1[C:16]([CH3:15])=[N:17][N:18]([C:5](=[O:7])[CH3:6])[C:19]=1[CH3:22]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 971153,5-Dimethyl-4-iodo-1H-pyrazole

Product 1

HCID 534715801-(4-Iodo-3,5-dimethyl-1H-pyrazol-1-yl)ethanoneYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (0.51 mL, 5.4 mmol) and triethylamine (0.75 mL, 5.4 mmol) were added to a solution of 3,5-dimethyl-4-iodopyrazole (1 g, 4.5 mmol) in CH2Cl2. After 1 h the reaction mixture was partitioned between 1N HCl and EtOAc. The organic layer was washed with 1N HCl, saturated NaHCO3, brine, dried over Na2SO4, and concentrated to give the title compound as a white solid (1 g, 85%). 1H NMR (CDCl3): δ 2.27 (s, 3H), 2.60 (s, 3H), 2.66 (s, 3H).

Workup

  1. customAfter 1 h the reaction mixture was partitioned between 1N HCl and EtOAc
  2. washThe organic layer was washed with 1N HCl, saturated NaHCO3, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9bff387d10024f9591613e565833c3e8
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Linked notes

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