Regarding the synthesis of 2-mercaptobenzothiazole was written by Ivanova, V. A.;Shebuev, A. N.. And the article was included in Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation) in 1957.Application of 1843-21-6 This article mentions the following:
A series of preparations were made in an attempt to establish the progressive steps in the synthesis of 2-mercaptobenzothiazole (I) from PhNH2, CS2, and S at 250°. The reactions of PhNH2 and CS2 to form (PhNH)2CS (II) or PhNCS (III) and H2S are reversible. The former decompose above 160° to form the original substances and the latter, though stable, reacts with S to form I only in the presence of saponifying agents. Neither II nor III can, therefore, be intermediate steps in the synthesis of I (cf. Sebrell and Boord, C.A. 17, 3876; Bruni and Levi, C.A. 18, 2341). Their presence in the products at certain stages of the reaction is attributed to side reactions. Heating 2-aminothiophenol (IV) or 2,2′-diaminodiphenyl disulfide (V) with S failed to yield acylated compounds This was probably due to the rapid closing of the thiazole ring to give I. On the other hand, in an alk. solution, IV reacts with CS2 at 80° to give C13H10N2S3 which reacts with Zn dust and HCl to give 4,4′-dimercaptodiphenylthiourea. By analogy it was assumed that CS2 acylates the amino group of IV or V which pass into I. PhNH2, CS2, and S were heated in an autoclave 3 hrs. at 250-60° and then cooled to 20°. After treatment with dilute HCl and recrystallization from 50% EtOH, V was obtained, m. 93°. The absence of IV and the presence of a considerable quantity of anilinobenzothiazole (VI) in the products were noted. The absence of IV was ascribed to its oxidation by S; at 20° S dissolved in IV with a vigorous evolution of H2S and the formation of V. The presence of VI was ascribed to the reversible reaction PhNH2 + I ⇌ VI + H2S which is shifted to the left as the normal synthesis progresses and PhNH2 is used up. VI is not an intermediate in the synthesis of I. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Application of 1843-21-6).
N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) belongs to thiazole derivatives. Thiazoles in peptides or their ability to bind proteins, DNA and RNA has led to many synthetic studies and new applications. Electrophilic attack at nitrogen depends on the presence of electron density at nitrogen as well as the position and nature of substituent linked to the thiazole ring.Application of 1843-21-6
Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica