Reaction #2069980

Reaction equation

NaOH

4-fluorobenzamidine hydrochloride

perchloromethyl mercaptan

→

title compound

5-Chloro-3-(4-fluoro-phenyl)-[1,2,4]thiadiazole

Solvents

water

DCM

Conditions

Workup

1. 1
   Extractionextracted with DCM (20 mL)
2. 2
   DryingThe organic layer was dried (MgSO4)
3. 3
   Concentrationconcentrated

Procedure

To a suspension of 4-fluorobenzamidine hydrochloride (0.385 g) in DCM (5 mL) was added perchloromethyl mercaptan (0.219 mL). The resulting mixture was cooled to 0° C., treated with 6 N NaOH (2 mL) and stirred for 30 min. The resulting mixture was diluted with water (10 mL) and extracted with DCM (20 mL). The organic layer was dried (MgSO4) and concentrated. Chromatography of the residue (0-20% EtOAc-hexanes) gave the title compound as a yellow-orange solid (0.43 g).

Source