Reaktion #2080928

Reaktionsgleichung

1,1-Thiocarbonyldiimidazole

4-{2-[(2-hydroxy-1,1-dimethylethyl)amino]-1,3-thiazol-4-yl}benzonitrile

→

title compound

Ausbeute 11.4%

4-[2-(4,4-Dimethyl-2-thioxo-1,3-oxazolidin-3-yl)-1,3-thiazol-4-yl]benzonitrile

Ausbeute 11.4%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction was heated to reflux
2. 2
   workup.WAITAfter 12 h
3. 3
   Temperaturthe reaction was cooled to room temperature
4. 4
   Einengenconcentrated under reduced pressure
5. 5
   SonstigePurification of the residue by reverse phase HPLC
6. 6
   Sonstigeover 10 min

Vorschrift

1,1-Thiocarbonyldiimidazole (652 mg, 3.6 mmol) was added to a solution of 4-{2-[(2-hydroxy-1,1-dimethylethyl)amino]-1,3-thiazol-4-yl}benzonitrile (1.0 g, 3.6 mmol), prepared in the previous step, in 60 mL of dry tetrahydrofuran at 0° C. The solution was allowed to warm to room temperature. After 2 h, starting material remained. The reaction was heated to reflux. After 12 h, the reaction was cooled to room temperature and concentrated under reduced pressure. Purification of the residue by reverse phase HPLC using a continuous gradient of 70-83% acetonitrile-water over 10 min gave the title compound (130 mg, 11%) as a tan solid. mp>240° C. (dec.)

Quelle