Potassium Iodide → 3-(2-Phenyl-4-thiazolylmethoxy)benzenacetonitrile

HRID 330377Notes

Reaction equation

HRID 330377 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]#[N:10])[CH:5]=[CH:6][CH:7]=1.Cl.Cl[CH2:13][C:14]1[N:15]=[C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[S:17][CH:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>CC(C)=O>[C:19]1([C:16]2[S:17][CH:18]=[C:14]([CH2:13][O:1][C:2]3[CH:3]=[C:4]([CH2:8][C:9]#[N:10])[CH:5]=[CH:6][CH:7]=3)[N:15]=2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 137810422-(3-Hydroxyphenyl)acetonitrileHCID 162436754-(Chloromethyl)-2-phenyl-1,3-thiazole hydrochloride

Product 1

HCID 144799853-(2-Phenyl-4-thiazolylmethoxy)benzenacetonitrileYield 43.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 14.0 g (0.105 mol) of 3-hydroxyphenylacetonitrile in 500 ml of acetone were added 25.9 g (0.105 mol) of 4-chloromethyl-2-phenylthiazole hydrochloride and 34.2 g (0.105 mol) of cesium carbonate and 1 g of potassium iodide and the slurry is heated to reflux for 20 hours. The mixture is filtered and the solution is concentrated in vacuo to obtain crystals. Recrystallization from ethyl acetate gives 14.0 g (43%) crystals, m.p. 108°-110° C. The product is used without further purification in subsequent reactions.

Workup

  1. temperaturethe slurry is heated
  2. temperatureto reflux for 20 hours
  3. filtrationThe mixture is filtered
  4. concentrationthe solution is concentrated in vacuo
  5. customto obtain crystals
  6. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-e72db77afa1d4b65bcd4a7c4ce9d20c5
Source dataset
uspto-grants-1990_01
Patent number
US04895953

Reaction notes

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