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13.29.1.1.2.7 Method 7: 1,2,3,4-Thiatriazole-5-thiol from Carbon Disulfide and Azide Salts

DOI: 10.1055/sos-SD-013-01396

Begtrup, M.Science of Synthesis, (200413841.

The thiatriazole-5-thiol 19 is a fairly strong acid and its salts are readily obtained from the water-soluble alkali and alkaline earth azides with carbon disulfide at 40°C (Scheme 18).[‌53‌‌56‌] The salts should be handled with care. The potassium salt may explode violently when spread on a porous plate[‌53‌] and the slightly soluble heavy-metal salts are very sensitive to shock even under water.[‌57‌] 1,2,3,4-Thiatriazole-5-thiol (19) can be generated by addition of concentrated hydrochloric acid to a chilled solution of the sodium salt, obtained as a white or slightly yellow crystalline compound.[‌58‌] The thiatriazole 19 was conveniently converted into its more stable sodium salt by neutralization with 30% aqueous sodium hydroxide to the phenolphthalein end point.[‌59‌] An improved method for the preparation and storage of sodium thiatriazole-5-thiolate has been reported.[‌57‌] The structure of the sodium salt was determined in 2000 by X-ray analysis.[‌60‌] The free acid 19 can also, less conveniently, be prepared from hydrazoic acid and carbon disulfide.[‌61‌]

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