Water → HCID 22065144, Verbindung

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-Eintrag

ord-9d74ab7b9e1f4d5e98c1f203405e6aee

Quelldatensatz

uspto-grants-2004_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06770665B2