HCID 86684915, compound → HCID 86684914, compound

Temperature

100 °C

4-(4-tert-Butylsulfanyl-3-trifluoromethyl-phenyl)-1-methyl-1H-pyrazole (40.0 g, 127 mmol) was suspended in hydrochloric acid (25% w/w, 780 mL) and stirred at 100° C. under reflux. Part of the hydrochloric acid was distilled off (ca. 80 mL). After the reaction was complete as shown by HPLC, it was cooled to 85° C., water (240 mL) was added, and the mixture was cooled further to 20° C. The pH was adjusted to 4.0 by addition of a solution of sodium hydroxide (32% w/w, ca. 480 mL) in water (960 mL). The aqueous phase was extracted with 2-methyltetrahydrofuran (2×320 mL), the combined organic extracts were washed with a solution of sodium chloride (40.0 g) in water (400 mL) and concentrated in vacuo. The residue was redissolved in tetrahydrofuran (260 mL), concentrated in vacuo, dissolved again in tetrahydrofuran (110 mL) and filtered in order to remove inorganic salts. The precipitate was washed with tetrahydrofuran (30 mL) and the combined filtrate was concentrated in vacuo to obtain the title compound as light brown solid (32.4 g, 98.6%), that was used without further purification in the next step.

1. temperatureunder reflux
2. distillationPart of the hydrochloric acid was distilled off (ca. 80 mL)
3. temperaturewas cooled to 85° C.
4. additionwater (240 mL) was added
5. temperaturethe mixture was cooled further to 20° C
6. additionThe pH was adjusted to 4.0 by addition of a solution of sodium hydroxide (32% w/w, ca. 480 mL) in water (960 mL)
7. extractionThe aqueous phase was extracted with 2-methyltetrahydrofuran (2×320 mL)
8. washthe combined organic extracts were washed with a solution of sodium chloride (40.0 g) in water (400 mL)
9. concentrationconcentrated in vacuo
10. dissolutionThe residue was redissolved in tetrahydrofuran (260 mL)
11. concentrationconcentrated in vacuo
12. dissolutiondissolved again in tetrahydrofuran (110 mL)
13. filtrationfiltered in order
14. customto remove inorganic salts
15. washThe precipitate was washed with tetrahydrofuran (30 mL)
16. concentrationthe combined filtrate was concentrated in vacuo

ORD record

ord-6dc47b1adb864ddfb9ebde847d89a4ba

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08796471B2