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

To a solution of 2-methylpropanimidamide hydrochloride (2.00 g, 16.3 mmol) and perchloromethyl mercaptan (1.75 ml, 16.3 mmol) in dichloromethane (40 ml) was added dropwise a solution of sodium hydroxide (3.26 g, 81.5 mmol) in water (6 ml) under ice-cooling. Then, the reaction mixture was stirred under ice-cooling for 1 hour and at room temperature for 1 hour. The organic layer was separated, washed with water, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to give 1.22 g (46.2%) of the desired product as an oil.

1. temperaturecooling
2. customThe organic layer was separated
3. washwashed with water
4. dry with materialdried over anhydrous magnesium sulfate
5. distillationThe solvent was distilled off under reduced pressure
6. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

ORD record

ord-9b8d7358433f465bbecebb848273a14c

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07851473B2