Water → 4-(4-Chlorothiophen-2-yl)-1,3-thiazol-2-amine

To a solution of 4.18 g of 4-chloro-2-acetylthiophene in 30 ml of diethylether, 1.5 ml of bromine was added under ice cooling, and the mixture was stirred at room temperature for 2 hours. Water was added to the reaction solution, and the organic phase was extracted. The obtained organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain brominated compound. To a solution of the brominated compound in 30 ml of EtOH, 2.1 g of thiourea was added at room temperature, and the mixture was stirred at 80° C. overnight. The precipitate was filtered, and obtained solution was evaporated under reduced pressure. Chloroform was added and then an organic layer was washed with aqueous potassium carbonate and brine, and dried over sodium sulfate. The residue obtained by the evaporation of the solvent under reduced pressure was washed with hexane:EtOAc=1:1 to obtain 2.57 g of 2-amino-4-(4-chlorothiophen-2-yl)thiazole.

1. extractionthe organic phase was extracted
2. washThe obtained organic layer was washed with brine
3. dry with materialdried over anhydrous sodium sulfate
4. customThe solvent was evaporated under reduced pressure
5. customto obtain brominated compound
6. stirringthe mixture was stirred at 80° C. overnight
7. filtrationThe precipitate was filtered
8. customobtained solution
9. customwas evaporated under reduced pressure
10. additionChloroform was added
11. washan organic layer was washed with aqueous potassium carbonate and brine
12. dry with materialdried over sodium sulfate
13. customThe residue obtained by the evaporation of the solvent under reduced pressure
14. washwas washed with hexane

ORD record

ord-4e79a75242884699852bc3f66e360c97

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07638536B2