Water → 1-(4-Iodo-1H-pyrazol-1-yl)ethan-1-one

HRID 1850072Notes

Reaction equation

HRID 1850072 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].C(N(CC)CC)C.[I:12][C:13]1[CH:14]=[N:15][NH:16][CH:17]=1.O>ClCCl>[C:1]([N:15]1[CH:14]=[C:13]([I:12])[CH:17]=[N:16]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 770224-Iodopyrazole

Product 1

HCID 153665251-(4-Iodo-1H-pyrazol-1-yl)ethan-1-oneYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetyl chloride (38.2 mL, 1.07 equiv) and triethylamine (86 mL, 1.2 equiv) were added at 0° C. to a solution of 4-iodo-1H-pyrazole (100 g, 0.515 mol) in dichloromethane (1 L). The mixture was stirred overnight at room temperature. The reaction mixture was poured into water. The aqueous layer was extracted with dichloromethane. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate (Na2SO4), and filtered. The residue obtained by concentration was purified by silica gel column chromatography (Hexane/EtOAc 20:1 to 1:1) to give N-acetyl 4-iodo-1H-pyrazole as a solid (110 g, 91%).

Workup

  1. extractionThe aqueous layer was extracted with dichloromethane
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over anhydrous sodium sulfate (Na2SO4)
  4. filtrationfiltered
  5. customThe residue obtained by concentration
  6. customwas purified by silica gel column chromatography (Hexane/EtOAc 20:1 to 1:1)

Sources & evidence

ORD record
ord-ddddfcb7cfc44c269a57bd11b8bc8511
Source dataset
uspto-grants-2015_02
Patent number
US08957066B2

Reaction notes

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