Phosgene → (S)-3-chloro-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolinium chloride

Participants

Reaction Conditions

Reaction Steps

A solution (20 cc.) containing 2 mols per liter of phosgene in toluene, is added dropwise, in the absence of moisture, whilst stirring and at a temperature of about 20° C ., to a solution of (S)-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinoline-3-thione (2.2 g.) in tetrahydrofuran (25 cc.). The mixture becomes cloudy after 15 minutes; it is stirred for 5 hours and then heated to 50° C. for 1 hour. The solvents are evaporated under reduced pressure (25 mm. Hg ) at 60° C. to give (S)-3-chloro-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolinium chloride (2.6 g.) in the form of a very hygroscopic white crystalline powder.

Provenance & Evidence