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