1,4-Dioxane → 5-Bromo-4-chloro-N-[(4-methoxyphenyl)methyl]-1,3-thiazol-2-amine

Temperature

75 °C

To a 250 mL round-bottomed flask was added 2,5-dibromo-4-chlorothiazole (5.9 g, 21 mmol), p-dioxane (50 mL, 587 mmol), and 4-methoxybenzylamine (3 mL, 21 mmol). The solution was stirred at 75° C. for 4 hours. The reaction was cooled to room temperature, and the solvent was removed. The residue was dissolved in EtOAc and washed with saturated NaHCO3 (1×25 mL), saturated sodium chloride (1×25 mL), water (1×25 mL), and dried over Na2SO4, filtered and concentrated in vacuum. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Redi-Sep® pre-packed silica gel column (40 g), eluting with a gradient (5%→50% EtOAc in hexane) to provide N-(4-methoxybenzyl)-5-bromo-4-chlorothiazol-2-amine (5.5 g, 80% yield), m/z (%): 334.1 (100%, M++H).

1. temperatureThe reaction was cooled to room temperature
2. customthe solvent was removed
3. dissolutionThe residue was dissolved in EtOAc
4. washwashed with saturated NaHCO3 (1×25 mL), saturated sodium chloride (1×25 mL), water (1×25 mL)
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated in vacuum
8. customchromatographed through a Redi-Sep® pre-packed silica gel column (40 g)
9. washeluting with a gradient (5%→50% EtOAc in hexane)

ORD record

ord-6a757df7ae674e638d121fdf32c70abe

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07514566B2