Water → HCID 12112402, compound

HRID 1792783Notes

Reaction equation

HRID 1792783 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:9][C:10]([CH:26]([CH3:28])[CH3:27])=[C:11]([CH2:13][CH2:14]OS(C2C=CC(C)=CC=2)(=O)=O)[N:12]=1.[I-:29].[Na+].O>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:9][C:10]([CH:26]([CH3:28])[CH3:27])=[C:11]([CH2:13][CH2:14][I:29])[N:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 5238Sodium IodideHCID 12112401HCID 12112401, compound

Product 1

HCID 12112402HCID 12112402, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In acetone (2 mL) was dissolved 2-(2-chlorophenyl)-5-isopropyl-4-[2-(p-toluenesulfonyloxy)ethyl]oxazole (123 mg, 0.293 mmol). To the solution was added sodium iodide (176 mg, 1.17 mmol). The mixture was heated overnight under reflux. The reaction mixture was allowed to reach room temperature, poured into water, and extracted with ethyl acetate. The organic layer was successively washed with water and saturated brine, dried over sodium sulfate, filtered, and concentrated, to obtain the desired compound (105 mg, 96%).

Workup

  1. temperatureThe mixture was heated overnight
  2. temperatureunder reflux
  3. customto reach room temperature
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was successively washed with water and saturated brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-591dbc95e67f486b9e9789c5d5d37fd9
Source dataset
uspto-grants-2006_07
Patent number
US07078422B2

Reaction notes

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