Acetonitrile → [4-Butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-acetonitrile

HRID 2233549Notes

Reaction equation

HRID 2233549 reaction equation
[CH2:1]([C:5]1[N:6]=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[S:8][C:9]=1[CH2:10]Cl)[CH2:2][CH2:3][CH3:4].C([O-])(O)=O.[Na+].C(OCC)(=O)C.[C:33](#[N:35])C>[C-]#N.C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:1]([C:5]1[N:6]=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[S:8][C:9]=1[CH2:10][C:33]#[N:35])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 230893954-Butyl-5-chloromethyl-2-(4-trifluoromethyl-phenyl)-thiazole

Product 1

HCID 59296158[4-Butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-acetonitrile

Reagents, catalysts & solvents 1

HCID 165872Tetrabutylammonium CyanideCatalyst

Procedure

3.0 g 4-Butyl-5-chloromethyl-2-(4-trifluoromethyl-phenyl)-thiazole were dissolved in 50 ml acetonitrile. To this solution was added 2.89 g tetrabutylammoniumcyanide. The reaction mixture was stirred at room temperature for thirty minutes. Then a mixture of saturated NaHCO3 solution, ice and ethyl acetate was added. The aqueous phase was separated and extracted three times with portions of 30 ml ethylacetate. The combined organic layers were washed with ice cold water and brine and dried over MgSO4. The solvent was removed in vacuo. The residue was purified by flash chromatography with the eluent n-heptane:ethyl acetate=5:1 to provide 1.1 g [4-Butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-acetonitrile as oil.

Workup

  1. additionwas added
  2. customThe aqueous phase was separated
  3. extractionextracted three times with portions of 30 ml ethylacetate
  4. washThe combined organic layers were washed with ice cold water and brine
  5. dry with materialdried over MgSO4
  6. customThe solvent was removed in vacuo
  7. customThe residue was purified by flash chromatography with the eluent n-heptane

Sources & evidence

ORD record
ord-d97cda0619c54081b09a9165d920a333
Source dataset
uspto-grants-2010_05
Patent number
US07709509B2

Reaction notes

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