Reaction #2254151

Reaction equation

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

Yield 91.1%

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   Temperaturethe reaction mixture was heated
2. 2
   Temperatureunder reflux for 1 h
3. 3
   Otherthe 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
   Dryingthe organic phase was dried over sodium sulphate
7. 7
   Filtrationfiltered
8. 8
   Otherthe solvent was removed under reduced pressure

Procedure

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