Sodium Cyanide → 2-(2-tert-Butyl-1,3-oxazol-4-yl)acetonitrile

HRID 230091Notes

Reaction equation

HRID 230091 reaction equation
[C-:1]#[N:2].[Na+].[C:4]([C:8]1[O:9][CH:10]=[C:11]([CH2:13]Cl)[N:12]=1)([CH3:7])([CH3:6])[CH3:5].[OH-].[Na+]>CS(C)=O>[C:4]([C:8]1[O:9][CH:10]=[C:11]([CH2:13][C:1]#[N:2])[N:12]=1)([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 8929Sodium CyanideHCID 14798Sodium HydroxideHCID 221695102-tert-Butyl-4-(chloromethyl)-1,3-oxazole

Product 1

HCID 221695172-(2-tert-Butyl-1,3-oxazol-4-yl)acetonitrileYield 92.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
65 °C

Procedure

6.2 g of sodium cyanide was weighed, 50 ml of dimethylsulfoxide was added thereto, and a dimethylsulfoxide solution of 16.9 g of 2-tert-butyl-4-chloromethyloxazole was dropwise added thereto, and heated on an oil bath at 65° C. for 1 hour with stirring. After the resulting product was cooled to room temperature, 150 ml of a dilute aqueous solution of sodium hydroxide was added thereto, and extracted with toluene. The organic layer was fully washed with water, and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 14.8 g of 2-tert-butyl-4-cyanomethyloxazole.

Workup

  1. temperatureAfter the resulting product was cooled to room temperature
  2. extractionextracted with toluene
  3. washThe organic layer was fully washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-c3fd6434cb38404fbbdf44c9203b3a5d
Source dataset
uspto-grants-2009_07
Patent number
US07566683B2

Reaction notes

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