Sodium Chloride → HCID 18445852, compound

HRID 270936Notes

Reaction equation

HRID 270936 reaction equation
COC(=O)[CH:4]([C:13]1[CH:18]=[CH:17][C:16]([I:19])=[CH:15][CH:14]=1)[C:5]([CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:6].[Cl-].[Na+]>CS(C)=O.O>[CH:7]1([C:5](=[O:6])[CH2:4][C:13]2[CH:14]=[CH:15][C:16]([I:19])=[CH:17][CH:18]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

5

Reactant 2

HCID 5234Sodium ChlorideHCID 58825030HCID 58825030, compound

Product 1

HCID 18445852HCID 18445852, compoundYield 96.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Conditions

Temperature
150 °C

Procedure

According to a modified literature procedure (Collins, I. et al J. Med. Chem. 2002, 45, 1887-1900) a solution of 5.06 g (13.1 mmol) of 3-cyclohexyl-2-(4-iodo-phenyl)-3-oxo-propionic acid methyl ester in 80 mL of dimethylsulfoxide (DMSO) was added a solution of 1.53 g (26.2 mmol) of sodium chloride (NaCl) in 5.8 mL of water (H2O), and the resulting mixture was heated at 150° C. for 3 h during which time a white solid formed. The reaction mixture was cooled to rt, poured into 500 mL of water, and extracted thoroughly with ethyl acetate. The combined organic extracts were washed with water (3 times), brine, dried over sodium sulfate and concentrated to give 4.13 g (96% yield) of desired 1-cyclohexyl-2-(4-iodo-phenyl)-ethanone as a yellow solid as indicated by 1H NMR (containing small traces of impurities). The product was used without any further purification in the next step.

Workup

  1. customformed
  2. temperatureThe reaction mixture was cooled to rt
  3. extractionextracted thoroughly with ethyl acetate
  4. washThe combined organic extracts were washed with water (3 times), brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-59d0f38539f442018d46c5cb5b1c6dd1
Source dataset
uspto-grants-2008_11
Patent number
US07449488B2

Reaction notes

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