Diethyl Ether → HCID 58609772, compound

2-Chloro-phenol (1.7 mL, 16.0 mmol) was dissolved in a mixture of 36 mL of tetrhydrofuran (THF) and 4 mL of N,N-dimethylformamide (DMF). Sodium hydride (60% dispersion in oil, 0.700 g, 17.5 mmol) was added and the reaction was stirred for 5 minutes under an atmosphere of nitrogen. A solution of 5-bromo-thiazol-2-ylamine hydrobromide (2.1 g, 8.0 mmol) in 18 mL of THF and 2 mL of DMF was slowly added to the reaction mixture. The mixture was allowed to stir for 10 minutes and then 100 mL of ether was added. The reaction mixture was washed with 1N sodium hydroxide. The organic layer was dried over sodium sulfate, filtered, and evaporated to dryness. The crude product was purified on silica gel using a gradient of 50-99% ethyl acetate in hexanes to yield the product as a brown solid (0.3546 g, 1.564 mmol, 19%)

1. stirringto stir for 10 minutes
2. washThe reaction mixture was washed with 1N sodium hydroxide
3. dry with materialThe organic layer was dried over sodium sulfate
4. filtrationfiltered
5. customevaporated to dryness
6. customThe crude product was purified on silica gel using a gradient of 50-99% ethyl acetate in hexanes

ORD record

ord-4c55aa949e4347058b418d07c61d4f41

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08759335B2