Sodium Iodide → HCID 68593387, compound

HRID 1516613Notes

Reaction equation

HRID 1516613 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1)#[N:2].C(=O)([O-])[O-].[K+].[K+].[C:16]([O:19][CH2:20][CH2:21]Br)(=[O:18])[CH3:17].[I-].[Na+]>CC(C)=O>[C:16]([O:19][CH2:20][CH2:21][O:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[N:2])[CH:4]=1)(=[O:18])[CH3:17]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 133943-CyanophenolHCID 135641-Acetoxy-2-bromoethane

Product 1

HCID 68593387HCID 68593387, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

3-Cyanophenol (10.1 g, 84.8 mmol) and potassium carbonate (19.5 g, 141 mmol) were suspended in acetone (280 ml), 2-bromoethyl acetate (7.8 ml, 70.7 mmol) was added, and the mixture was stirred at 50° C. for 8 hours. Sodium iodide (1.06 g, 7.07 mmol) was added to the reaction mixture, and the mixture was heated under reflux for two nights and concentrated under reduced pressure. The residue was diluted with ethyl acetate, and the mixture was washed with 1N sodium hydroxide, 1N hydrochloric acid, and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound without purification.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for two nights
  3. concentrationconcentrated under reduced pressure
  4. additionThe residue was diluted with ethyl acetate
  5. washthe mixture was washed with 1N sodium hydroxide, 1N hydrochloric acid, and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7f2d5ed55439419d950fe1a0a2adc813
Source dataset
uspto-grants-2012_07
Patent number
US08227506B2

Reaction notes

Loading…