Reaction #1583830

Reaction equation

2-methyl propanimidamide hydrochloride

trichloromethanesulfenyl chloride

sodium hydroxide

→

title compound

Yield 60.8%

5-chloro-3-(1-methylethyl)-1,2,4-thiadiazole

Yield 60.8%

Solvents

methylene chloride

Conditions

Workup

1. 1
   Temperatureto warm to room temperature
2. 2
   workup.STIRRINGstirred for an additional 3 h
3. 3
   workup.ADDITIONIce was added to the reaction mixture
4. 4
   Otherthe mixture was separated
5. 5
   Extractionthe aqueous layer was extracted with methylene chloride (3×25 mL)
6. 6
   DryingThe combined organic extracts were dried over magnesium sulfate
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated under reduced pressure
9. 9
   OtherThe resulting residue was purified by medium pressure liquid chromatography (0 to 100% gradient of ethyl acetate in hexanes as eluant)

Procedure

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).

Source