Sodium Cyanide → (2-Cyclohexyl-5-methyl-oxazol-4-yl)-acetonitrile

HRID 2215205Notes

Reaction equation

HRID 2215205 reaction equation
[C-:1]#[N:2].[Na+].Cl[CH2:5][C:6]1[N:7]=[C:8]([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[O:9][C:10]=1[CH3:11]>CS(C)=O>[CH:12]1([C:8]2[O:9][C:10]([CH3:11])=[C:6]([CH2:5][C:1]#[N:2])[N:7]=2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 219495724-Chloromethyl-2-cyclohexyl-5-methyl-oxazole

Product 1

HCID 15343904(2-Cyclohexyl-5-methyl-oxazol-4-yl)-acetonitrileYield 48.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To 1.464 g of NaCN (29.88 mmol), dissolved in 20 ml of DMSO, was slowly added via dropping funnel 4.12 g of the above prepared 4-chloromethyl-2-cyclohexyl-5-methyl-oxazole (19.28 mmol) at such a rate that the internal temperature stayed at 25–30°. Stirring was continued for additional 2 h at 35°. The reaction mixture was then poured onto crashed ice/AcOEt, the organic layer washed with water, dried over sodium sulfate, and evaporated to dryness. Flash chromatography (SiO2, hexane/AcOEt=8/2) gave 1.900 g of the title compound as colorless liquid.

Workup

  1. additionwas slowly added
  2. customstayed at 25–30°
  3. additionThe reaction mixture was then poured
  4. washthe organic layer washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-241ca668a50146a28134111ba19ec422
Source dataset
uspto-grants-2006_09
Patent number
US07109225B2

Reaction notes

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