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

HRID 858565

Reaction equation

HRID 858565 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 1 N HCl and EtOAc. The organic layer was washed with 1 N HCl, saturated NaHCO3, brine, dried over Na2SO4, and concentrated to give the title compound as a white solid (1 g, 85%).

Workup

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

Sources & evidence

ORD record
ord-451e09891b4444e4a3945325c8d69f96
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Linked notes

Loading…