74351-57-8

Upstream product

• 1779-81-3 4,5-Dihydro-thiazol-2-ylamin 
• 4859-07-8 3-chloro-5-phenyl-1,2-dithiol-1-ium chloride 
• 827-42-9 5-phenyl-3H-1,2-dithiol-3-one 
• 934-32-7 1H-benzimidazol-2-amine 

Relevant academic research and scientific papers

Studies of Heterocyclic Compounds. Part 28. Condensation of 3-Substituted 5-Phenyl-1,2-dithiolylium Salts with 2-Amino-N-heterocycles

3-Chloro-5-phenyl-1,2-dithiolylium chloride condenses in ethanol with 2-amino-N-heterocycles at the amino-group to yield yellow compounds; in many instances reaction occurs also at the ring nitrogen atom yielding orange compounds. 2-Amino-Δ2-thiazoline, 2-aminothiazole, 2-aminopyridine and its monomethyl derivatives, 2-amino-4,6-dimethylpyridine ,2-aminopyrimidine, and 2-aminobenzimidazole all underwent reaction at the amino-group to give the corresponding yellow 2-(5-phenyl-1,2-dithiol-3-ylidenamino)-N-heterocycles. 2-Amino-Δ2-thiazoline, 2-aminothiazole, 2-aminopyridine, 2-amino-3-methylpyridine, 2-amino-4-methylpyridine,and 2-amino-5-methylpyridine also underwent reaction at the ring nitrogen atom to give in low yield 4,5-dihydro-3-thiobenzoylmethylene-3H -thiazolothiadiazole, 3-thiobenzoylmethylene-3H-thiazolothiadiazole, and 3-thiobenzoylmethylene-3H-pyridothiadiazole and its 7-,6-,and 5-methyl derivatives, respectively,as polar orange compounds.The condensations of 3-methoxy-5-phenyl-1,2-dithiolylium fluorosulphonate with 2-amino-Δ2-thiazoline, 2-aminothiazole, and 2-amino-4-methylpyridine were studied.Condensation of 4-methyl-2-tricloromethylthioaminopyridine with benzoylacetic acid in dimethylformamide in the presence of triethylamine gave 6-methyl-3H-pyridothiadiazol-3-one (main prduct) and 6-methyl-3-benzoylmethylene-3H-pyridothiadiazole.Thionation of the latter with tetraphosphorous decasulphide in pyridine gave 6-methyl-3-thiobenzoylmethylene-3H-pyridothiadiazole.The results of 1H n.m.r. spectral studies, and of X-ray crystallographic studies by other workers, are discussed in relation to the structure of the yellow and the orange series of condesation products.It is proposed that the 3-thiobenzoylmethylene-3H-thiazolothiadiazoles and the 3-thiobenzoylmethylene-3H-pyridothiadiazoles, whose formation involves an S-S -> S-N bond switch, are formed via 3H-6,6aλ4-dithia-1,3-diazapentalenes which are higer energy intermediates or transition states. 3-Chloro-5-phenyl-1,2-dithiolylium chloride condensed with 2,6-diaminopyrimidine in a 2:1 ratio to give an orange and a polar red product for which structures are proposed.

THE STRUCTURE OF 5,6-DIHYDRO-3-THIOBENZOYLMETHYLENE-3H-THIAZOLOTHIADIAZOLE

C12H10N2S3, monoclinic, C2/c, a = 23.316 (11), b = 8.187 (11), c = 13.127 (10) Angstroem, β = 103.73 (5) deg, U = 2434.28 Angstroem3, Mr = 278.40, Dc = 1.519 Mg m-3 for Z = 8, F(000) = 1152.00, Mo Kα radiation, λ = 0.71069 Angstroem, μ(Mo Kα) = 0.521 mm-1; R = 0.088 for 1162 reflections.The title compound does not contain a hypervalent S atom.