Acetonitrile → HCID 59296146, compound

HRID 2233577Notes

Reaction equation

HRID 2233577 reaction equation
[CH2:1]([C:5]1[N:6]=[C:7]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)[S:8][C:9]=1[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18]Cl)=[C:14]([Cl:20])[CH:13]=1)[CH2:2][CH2:3][CH3:4].C([O-])(O)=O.[Na+].C(OCC)(=O)C.[C:42](#[N:44])C>[C-]#N.C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:1]([C:5]1[N:6]=[C:7]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)[S:8][C:9]=1[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:42]#[N:44])=[C:14]([Cl:20])[CH:13]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 59296175HCID 59296175, compound

Product 1

HCID 59296146HCID 59296146, compound

Reagents, catalysts & solvents 1

HCID 165872Tetrabutylammonium CyanideCatalyst

Procedure

3.1 g crude 4-Butyl-5-(3-chloro-4-chloromethyl-phenoxymethyl)-2-(4-trifluoromethyl-phenyl)-thiazole was dissolved in 50 ml acetonitrile. 2.0 g tetrabutylammonium cyanide were added and the reaction mixture stirred at room temperature for one hour. 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=4:1 to provide 2.2 g {4-[4-Butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-chloro-phenyl}-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-b20cd05b5aa045f79438e92bfc91cdee
Source dataset
uspto-grants-2010_05
Patent number
US07709509B2

Reaction notes

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