Réaction #1147088

Équation de réaction

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

2-imino-4-thiobiuret

→

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

Rendement 74.7%

Solvants

ethanol

Conditions de réaction

Traitement

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

Mode opératoire

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).

Source