N-bromobutanimide → 2-(2-Amino-1,3-thiazol-5-yl)ethan-1-ol

Temperature

0 °C

To an ice cold suspension of NBS (1.182 g, 6.72 mmol) in water (8 mL) was added 2,3-dihyofuran (0.75 mL, 9.92 mmol) slowly. The resulting solution was stirred at 0° C. for 1 h, followed by addition of thiourea (0.505 g, 6.63 mmol). The mixture was heated under reflux under nitrogen atmosphere overnight to form a yellow clear solution. The mixture was extracted with EtOAc (3×5 mL) and the aqueous solution was treated with ammonium hydroxide to pH 12. The solution was extracted with CH2Cl2 (2×5 mL), followed by extraction with EtOAc (8×10 mL). The CH2Cl2 layer contains small amount of product and large amount of impurities, which was discarded. The EtOAc layers were combined, dried, and concentrated to give 1.123 g 2-(2-amino-thiazol-5-yl)-ethanol

1. temperatureThe mixture was heated
2. temperatureunder reflux under nitrogen atmosphere overnight
3. customto form a yellow clear solution
4. extractionThe mixture was extracted with EtOAc (3×5 mL)
5. additionthe aqueous solution was treated with ammonium hydroxide to pH 12
6. extractionThe solution was extracted with CH2Cl2 (2×5 mL)
7. extractionfollowed by extraction with EtOAc (8×10 mL)
8. customdried
9. concentrationconcentrated

ORD record

ord-48bc12f0657a4999a7d5c88dc76e13c4

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08093266B2