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

HRID 2215190Notes

Reaction equation

HRID 2215190 reaction equation
[C-:1]#[N:2].[Na+].[C:4]([C:8]1[O:9][C:10]([CH3:15])=[C:11]([CH2:13]Cl)[N:12]=1)([CH3:7])([CH3:6])[CH3:5]>CS(C)=O>[C:4]([C:8]1[O:9][C:10]([CH3:15])=[C:11]([CH2:13][C:1]#[N:2])[N:12]=1)([CH3:7])([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 219495892-Tert-butyl-4-chloromethyl-5-methyl-oxazole

Product 1

HCID 11506550(2-tert-Butyl-5-methyl-oxazol-4-yl)-acetonitrileYield 98.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To 5.72 g of NaCN (116.8 mmol), dissolved in 77 ml of DMSO, was slowly added via dropping funnel 14.14 g of the above prepared 2-tert-butyl-4-chloromethyl-5-methyl-oxazole (75.3 mmol) at such a rate that the internal temperature stayed at 25–30°. Stirring was continued for an additional 1.5 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. Thereby, 13.19 g of the title product was obtained, which was used without further purification for the next step.

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-60b5ee38ab024a64afabe40da5717d94
Source dataset
uspto-grants-2006_09
Patent number
US07109225B2

Reaction notes

Loading…