Sodium Cyanide → [5-Methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-yl]-acetonitrile

HRID 479131Notes

Reaction equation

HRID 479131 reaction equation
[C-:1]#[N:2].[Na+].Cl[CH2:5][C:6]1[N:7]=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[O:9][C:10]=1[CH3:11]>CS(C)=O>[CH3:11][C:10]1[O:9][C:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)=[N:7][C:6]=1[CH2:5][C:1]#[N:2]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 102363332-(4-Trifluoromethylphenyl)-4-chloromethyl-5-methyloxazole

Product 1

HCID 18003422[5-Methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-yl]-acetonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To 5.39 g of NaCN (110 mol), dissolved in 72 ml of DMSO, was added via dropping funnel a solution of 19.57 g of the above prepared 4-chloromethyl-5-methyl-2-(4-trifluoromethyl-phenyl)-oxazole in 144 ml of DMSO (slightly exothermic). The reaction mixture was then kept for 1 h at 35° C. and 40° C. for 1 night. The reaction mixture was then poured onto crashed ice/AcOEt, the organic layer washed with water and brine, dried over magnesium sulfate, and evaporated to dryness. Flash chromatography (SiO2, hexane/AcOEt=8/2) delivered 8.81 g of the title compound as light yellow crystals of mp. 85-86°.

Workup

  1. additionwas added
  2. additionThe reaction mixture was then poured
  3. washthe organic layer washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-5510624caeca4c8c9df38b41fd26b79e
Source dataset
uspto-grants-2003_11
Patent number
US06642389B2

Reaction notes

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