Reacción #1147088

Ecuación de reacción

2-chloro-1-(4-methylpyridin-2-yl)propan-1-one

2-imino-4-thiobiuret

→

2-guanidino-5-methyl-4-(4-methylpyridin-2-yl)thiazole

Rendimiento 74.7%

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture was refluxed for 2 hours
2. 2
   Otrothe solvent was evaporated under reduced pressure
3. 3
   workup.ADDITIONTo the residue were added ethyl acetate
4. 4
   OtroThe ethyl acetate layer was separated
5. 5
   Lavadowashed with brine
6. 6
   Secadodried over sodium sulfate
7. 7
   Otroevaporated under reduced pressure
8. 8
   OtroThe residue was purified by column chromatography (silica gel 25 g, dichloromethane:methanol:triethylamine=80:10:1)

Procedimiento

To a solution of 2-chloro-1-(4-methylpyridin-2-yl)propan-1-one (0.4 g) in ethanol (5 ml) was added 2-imino-4-thiobiuret (257 mg). The mixture was refluxed for 2 hours, and the solvent was evaporated under reduced pressure. To the residue were added ethyl acetate and a saturated aqueous sodium hydrogencarbonate solution. The ethyl acetate layer was separated, washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 25 g, dichloromethane:methanol:triethylamine=80:10:1) to give 2-guanidino-5-methyl-4-(4-methylpyridin-2-yl)thiazole (402 mg).

Fuente