Water → HCID 22065144, compound

Temperature

45 °C

A suspension of 3-(2-chloro-6-fluorophenyl)-1-methyl-5-(4-methylthien-3-yl)-1H-1,2,4-triazole (2.35 g, 7.6 mmol) in glacial acetic acid (15 mL) was heated to 45° C. in order to effect solubilization. After cooling to 10° C., a solution of bromine (1.34 g, 0.43 mL, 8.4 mmol) in glacial acetic acid (4 mL) was added and the thick gel formed was stirred for 14 hours at room temperature. The reaction mixture was poured into cold water (100 mL) and extracted with ether (3×70 mL). The combined ethereal extracts were washed with water (100 mL), saturated aqueous sodium bicarbonate (2×100 mL), aqueous sodium bisulphite (10% solution, 300 mL) and brine (100 mL), dried over magnesium sulphate and concentrated under reduced pressure. Recrystallisation from ethyl acetate/hexane afforded yellow cubes. The mother liquor was chromatographed over silica gel to afford the product as colorless cubes (2.6 g, 89%): mp 133-134° C.; 1H NMR (CDCl3) δ 7.51 (s, 1H), 7.29-7.39 (m, 2H), 7.11 (t, 1H), 3.98 (s, 3H), 2.27 (s, 3H); EI/MS 386 m/e (M+).

1. temperatureAfter cooling to 10° C.
2. customthe thick gel formed
3. extractionextracted with ether (3×70 mL)
4. washThe combined ethereal extracts were washed with water (100 mL), saturated aqueous sodium bicarbonate (2×100 mL), aqueous sodium bisulphite (10% solution, 300 mL) and brine (100 mL)
5. dry with materialdried over magnesium sulphate
6. concentrationconcentrated under reduced pressure
7. customRecrystallisation from ethyl acetate/hexane afforded yellow cubes
8. customThe mother liquor was chromatographed over silica gel
9. customto afford the product as colorless cubes (2.6 g, 89%)

ORD record

ord-5d71e82ae61b4882ba1c9a91e96e9ced

Source dataset

uspto-grants-2005_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06949576B2