Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Journal of Organic Chemistry called Reactions in the thiazole series. I. Reactions of 2-chlorobenzothiazoles with thioureas, Author is Scott, Winfield; Watt, George W., which mentions a compound: 2407-11-6, SMILESS is O=[N+](C1=CC=C2N=C(Cl)SC2=C1)[O-], Molecular C7H3ClN2O2S, Product Details of 2407-11-6.
N-Methylenecyclohexylamine, melted on the water bath and treated with S in small portions, gives 37% of s-dicyclohexylthiourea (I), m. 179-80°; various modifications of the reaction did not materially increase the yield (maximum, 44%). The reaction of 1,1′-methylenebispiperidine and S in xylene did not give the expected s-dipentamethylenethiourea but there resulted 34% of piperidine pentamethylenedithiocarbamate, m. 172-3°, piperidine hydrosulfide, H2S and varying amounts of tarry products. The reaction of 2-chlorobenzothiazole (II) with thiourea, the allyl, Ph and o-tolyl derivatives gave 100, 100, 78 and 79%, resp., of 2-mercaptobenzothiazole (III); no reaction occurred with s-diphenyl- N,N-dimethyl-N’-phenyl-(IV), N,N-pentamethylene-N’-phenyl derivatives and I. II and N,N’-o-phenylenethiourea give the addition compound, C14H10ClN3S2, m. 233-4° (decomposition), in 86% yield when refluxed 1 hr. in EtOH. The yield of the 6-NO2 derivative of III, m. 225-7°, from the 6-NO2 derivative of II was: thiourea 100, allyl- 94, Ph-92, o-tolyl 93, s-di-Pr 49, I 94°, IV 0. A by-product in the reaction with IV is 2-dimethylamino-6-nitrobenzothiazole, m. 197.5-9°; Me2NH is probably formed by the decomposition of IV. The order of decreasing reactivity is thiourea > mono- > di- > trisubstituted.
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