Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 4-(4-iodo-1H-pyrazol-1-yl)cyclohexanone

HRID 1505683Notes

Reaction equation

HRID 1505683 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([N:11]3[CH:15]=[C:14]([I:16])[CH:13]=[N:12]3)[CH2:7][CH2:6]2)[O:4]CC1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CC(C)=O.O.CCOC(C)=O>[I:16][C:14]1[CH:13]=[N:12][N:11]([CH:8]2[CH2:7][CH2:6][C:5](=[O:4])[CH2:10][CH2:9]2)[CH:15]=1

Participants

6

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 595411251-(1,4-Dioxaspiro[4.5]dec-8-yl)-4-iodo-1H-pyrazole

Product 1

HCID 595411654-(4-iodo-1H-pyrazol-1-yl)cyclohexanoneYield 96%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-(1,4-Dioxa-spiro[4.5]dec-8-yl)-4-iodo-1H-pyrazole (2.81 g; 8.41 mmol; 1.00 eq.) and pyridinium para-toluenesulfonate (4.23 g; 16.8 mmol; 2.0 eq.) in acetone (40 mL) and water (40 mL) was heated at reflux O/N. It was then allowed to cool to RT and diluted with EtOAc. Aqueous phase was extracted with EtOAc (twice) and combined organic phases were washed with water and brine, dried over sodium sulftate, filtered and concentrated to give the title compound as a white powder (2.34 g, 96%). HPLC (Condition A): Rt 2.83 min (purity 99.2%). MS (ESI+): 291.1.

Workup

  1. temperatureat reflux O/N
  2. extractionAqueous phase was extracted with EtOAc (twice) and
  3. washwere washed with water and brine
  4. dry with materialdried over sodium sulftate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6efb66f8d5ba41a2b8b90b0a210b2978
Source dataset
uspto-grants-2015_12
Patent number
US09216991B2

Reaction notes

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