Réaction #2254151

Équation de réaction

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

Rendement 91.1%

Solvants

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   Températurethe reaction mixture was heated
2. 2
   Températureunder reflux for 1 h
3. 3
   Autrethe solvent was removed under reduced pressure
4. 4
   FiltrationThe precipitated product was filtered off with suction
5. 5
   ExtractionThe aqueous phase was extracted with dichloromethane
6. 6
   Séchagethe organic phase was dried over sodium sulphate
7. 7
   Filtrationfiltered
8. 8
   Autrethe solvent was removed under reduced pressure

Mode opératoire

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.

Source