Tert-Butyl nitrite → Ethyl 2-(2-cyanothiazol-4-yl)acetate

反応式

N(OC(C)(C)C)=O.[C:8]([Cu])#[N:9].N[C:12]1[S:13][CH:14]=[C:15]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:16]=1>C(#N)C>[C:8]([C:12]1[S:13][CH:14]=[C:15]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:16]=1)#[N:9]

参加物

実験手順

To a mixture of tert-butyl nitrite (10 mL, 80 mmol) and CuCN (7.28 g, 80 mmol) in anhydrous acetonitrile (30 mL) was added a solution of ethyl 2-(2-aminothiazol-4-yl)acetate (7.5 g, 40 mmol) in anhydrous acetonitrile (20 mL) dropwise over a period of 1 hour at 50° C., then the mixture was stirred at the temperature for 2.5 hours. The mixture was concentrated in vacuo and the residue was purified by a silica gel column chromatography (PETROLEUM ETHER/EtOAc (V/V)=25/1) to give the title compound as yellowish liquid (2 g, 25%). The compound was characterized by the following spectroscopic data: