Reacción #2254151

Ecuación de reacción

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

Rendimiento 91.1%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe reaction mixture was heated
2. 2
   Temperaturaunder reflux for 1 h
3. 3
   Otrothe solvent was removed under reduced pressure
4. 4
   FiltraciónThe precipitated product was filtered off with suction
5. 5
   ExtracciónThe aqueous phase was extracted with dichloromethane
6. 6
   Secadothe organic phase was dried over sodium sulphate
7. 7
   Filtraciónfiltered
8. 8
   Otrothe solvent was removed under reduced pressure

Procedimiento

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.

Fuente