Ethyl Acetate → 2-(2-Phenyl-1,3-thiazol-4-yl)acetonitrile

HRID 1822630Notes

Reaction equation

HRID 1822630 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[S:6][CH:7]=1.[C-:14]#[N:15].[K+].C(OCC)(=O)C>C(#N)C.C1OCCOC2C(=CC=CC=2)OCCOCCOC2C(=CC=CC=2)OC1>[C:14]([CH2:2][C:3]1[N:4]=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[S:6][CH:7]=1)#[N:15]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 9032Potassium CyanideHCID 2369694-(Chloromethyl)-2-phenyl-1,3-thiazole

Product 1

HCID 2238442-(2-Phenyl-1,3-thiazol-4-yl)acetonitrileYield 73.8%

Reagents, catalysts & solvents 2

HCID 26541Dibenzo-18-crown-6CatalystHCID 6342AcetonitrileSolvent

Procedure

1.39 g of 4-chloromethyl-2-phenylthiazole was dissolved in 10 ml of acetonitrile, and 0.65 g of potassium cyanide and 0.05 g of dibenzo-18-crown-6-ether were added thereto at room temperature, and then heated under reflux for 10 hours. After the temperature was returned to room temperature, ethyl acetate was added the resulting mixture, and the insoluble solid was removed through filtration. The resulting ethyl acetate solution was washed with saturated saline and water, and dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residual product was purified through silica gel column chromatography to obtain 0.98 g of 4-cyanomethyl-2-phenylthiazole from the fraction eluted with chloroform.

Workup

  1. temperatureunder reflux for 10 hours
  2. customwas returned to room temperature
  3. customthe insoluble solid was removed through filtration
  4. washThe resulting ethyl acetate solution was washed with saturated saline and water
  5. dry with materialdried over sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residual product was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-ebd5d394cf0543b1903f5e6f7615aef6
Source dataset
uspto-grants-2006_05
Patent number
US07037880B2

Reaction notes

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