Reaktion #2254151

Reaktionsgleichung

1,8-diazabicyclo[5.4.0]undec-7-ene

2-Bromo-1,3-thiazole-4-carboxylic acid

Methanesulphonamide

→

2-bromo-N-(methylsulphonyl)-1,3-thiazole-4-carboxamide

Ausbeute 91.1%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction mixture was heated
2. 2
   Temperaturunder reflux for 1 h
3. 3
   Sonstigethe solvent was removed under reduced pressure
4. 4
   FiltrationThe precipitated product was filtered off with suction
5. 5
   ExtraktionThe aqueous phase was extracted with dichloromethane
6. 6
   Trocknenthe organic phase was dried over sodium sulphate
7. 7
   Filtrationfiltered
8. 8
   Sonstigethe solvent was removed under reduced pressure

Vorschrift

2-Bromo-1,3-thiazole-4-carboxylic acid (0.8 g, 3.85 mmol) was initially charged in tetrahydrofuran (10 ml). N,N′-Carbonyldiimidazole (0.94 g, 5.77 mmol) was added and the reaction mixture was heated under reflux for 1 h. Methanesulphonamide (0.55 g, 5.77 mmol) was added and, after 10 min, 1,8-diazabicyclo[5.4.0]undec-7-ene (0.88 g, 5.77 mmol). The reaction mixture was stirred at room temperature for 16 h and then the solvent was removed under reduced pressure. The residue was taken up in water and acidified with hydrochloric acid. The precipitated product was filtered off with suction. The aqueous phase was extracted with dichloromethane; the organic phase was dried over sodium sulphate and filtered, and the solvent was removed under reduced pressure. This gave a total of 1.0 g (89% of theory) of 2-bromo-N-(methylsulphonyl)-1,3-thiazole-4-carboxamide.

Quelle