Cyclization products from amino-substituted Bunte salts was written by Caldwell, J. B.;Milligan, Brian;Swan, J. M.. And the article was included in Journal of the Chemical Society in 1963.Electric Literature of C13H10N2S This article mentions the following:
PhNCS (I) (14 g.) 8.0 g. H2NCH2CH2SSO3H (Ia), and 100 ml. 50% aqueous C5H5N stirred vigorously 1.5 hrs., the pH maintained at 9 by the addition of 10% NaOH, the whole evaporated in vacuo, and the residue extracted with boiling EtOH gave 9.0 g. PhNHCSNHCH2CH2SSO3Na (II), m. 177° (decomposition). To 2.75 g. II in 25 ml. H2O at 0° was added 25 ml. 10N HCl, the whole swept 1 hr. with N, and the pH adjusted to 7 to give 3-anilino-5,6-dihydro-1,2,4-dithiazine (III); picrate m. 195-9° (decomposition). Similarly, I and o-H2NC6H4SSO3H (IV) gave 76% IVa (R = H, R1 = PhNH), m. 160° (C6H6); I and 2,5-H2N(Me2N)C6H3SSO3H (V) gave 51% IVa (R = Me2N, R1 = PhNH), m. 173°; MeNCS (VI) and IV gave 56% IVa (R = H, R1 = MeNH), m. 139-40° (CCl4); VI and V gave 65% IVa (R = Me2N, R1 = MeNH), m. 148-50° (petr. ether). IV (1 g.), 5 ml. CS2, and 20 ml. 1:1 C5H5N-5% aqueous Na2CO3 refluxed 0.5 hr. gave 80% IVa (R = H, R1 = SH), m. 181°; V and CS2 gave IVa (R = Me2N, R1 = SH), m. 234°; and Ia and CS2 gave 2-thiazoline-2-thiol, m. 105-6°. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Electric Literature of C13H10N2S).
N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). The nitrogen in thiazole is sp2 hybridized and the lone pair of electrons localized on the nitrogen is less reactive due to increased aromatic character and decreased basicity. It is protonated and alkylated/acylated at nitrogen forming hydrochloride and quaternary thiazolium salt.Electric Literature of C13H10N2S
Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica