Trichloromethanesulfenyl chloride → 5-Chloro-3-(propan-2-yl)-1,2,4-thiadiazole

Temperatur

0 °C

To a mixture of 2-methyl propanimidamide hydrochloride (5.0 g, 40.8 mmol), trichloromethanesulfenyl chloride (7.14 g, 38.4 mmol) in methylene chloride (200 mL) at 0° C. was added dropwise an aqueous solution of sodium hydroxide (50%, 9.9 mL) over 20 minutes. The reaction mixture was stirred for 2 h at 0° C. and then was allowed to warm to room temperature, and stirred for an additional 3 h. Ice was added to the reaction mixture, the mixture was separated, and the aqueous layer was extracted with methylene chloride (3×25 mL). The combined organic extracts were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by medium pressure liquid chromatography (0 to 100% gradient of ethyl acetate in hexanes as eluant) to provide the title compound as a oil (3.8 g).

1. temperatureto warm to room temperature
2. stirringstirred for an additional 3 h
3. additionIce was added to the reaction mixture
4. customthe mixture was separated
5. extractionthe aqueous layer was extracted with methylene chloride (3×25 mL)
6. dry with materialThe combined organic extracts were dried over magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customThe resulting residue was purified by medium pressure liquid chromatography (0 to 100% gradient of ethyl acetate in hexanes as eluant)

ORD-Eintrag

ord-ea9f97223aea4491bd7056a3dd4b20cc

Quelldatensatz

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08822521B2