Potassium Iodide → HCID 23371333, compound

HRID 1735703Notes

Reaction equation

HRID 1735703 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[S:6][CH:7]=1.[OH:15][CH2:16][C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:18].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(O)C>[F:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[S:6][CH:7]=[C:3]([CH2:2][O:15][CH2:16][C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:18])[N:4]=2)=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 68490alpha-HydroxyacetophenoneHCID 21108384-(chloromethyl)-2-(4-fluorophenyl)-1,3-thiazole

Product 1

HCID 23371333HCID 23371333, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

11.2 g (0.05 mol) of 4-chloromethyl-2-(4-fluorophenyl) thiazole (see Example 4), 5.4 g (0.04 mol) of 2-hydroxyacetophenone, 7.5 g (0.055 mol) of potassium carbonate and 0.5 g of potassium iodide in 20 ml ethanol are refluxed for 24 hours. The mixture is filtered, the filtrate is concentrated, the residue is taken up in dichloromethane, the solution is extracted with dilute sodium hydroxide solution and then with water, and the organic phase is dried over MgSO4. Removal of the solvent by distillation under reduced pressure results in a solid residue which is washed with diisopropyl ether to give 9.7 g (59% yield) of 2-[2-(4-fluorophenyl)-4-thiazolylmethyloxy]acetophenone as yellowish crystals of melting point 104°-106° C.

Workup

  1. filtrationThe mixture is filtered
  2. concentrationthe filtrate is concentrated
  3. extractionthe solution is extracted with dilute sodium hydroxide solution
  4. dry with materialwith water, and the organic phase is dried over MgSO4
  5. customRemoval of the solvent
  6. distillationby distillation under reduced pressure
  7. customresults in a solid residue which
  8. washis washed with diisopropyl ether

Sources & evidence

ORD record
ord-6b7ee6a66c2a47a49a99a96d1d3bf3f4
Source dataset
uspto-grants-1996_07
Patent number
US05538940

Reaction notes

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