The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Benzothiazoles. VIII. Nitration of 2-substituted benzothiazoles》. Authors are Mizuno, Yoshihisa; Adachi, Kikuo; Nakamura, Kaname.The article about the compound:2-Chloro-6-nitrobenzo[d]thiazolecas:2407-11-6,SMILESS:O=[N+](C1=CC=C2N=C(Cl)SC2=C1)[O-]).Product Details of 2407-11-6. Through the article, more information about this compound (cas:2407-11-6) is conveyed.
NaOH (1 g.), 1 ml. water, 16 ml. EtOH, and 2 g. 2-methoxybenzothiazole (XI) boiled 15 min. on a steam bath, the solution cooled, poured into 80 ml. water, acidified with 5 ml. concentrated HCl, let stand overnight, and the precipitate filtered gave 1.6 g. (0.3 g. from the mother liquor) unchanged XI, m. 32-3°; (picrate, m. 100-1°); nitration of 2.1 g. of recovered XI gave 1.7 g. mono-NO2 derivative, m. 164-5°; nitration of 10 g. benzothiazole (XII) in 50 ml. H2SO4 with 5 ml. 98% H2SO4 and 4 ml. fuming HNO3 (d. 1.5) at 0°, the solution poured into ice water, filtered and dried, yielded 62% 6-O2N derivative (XIIIA) of XII, m. 170-2° and 9.1% 7-O2N derivative (XIIIB), m. 150-4°; similarly, 2-chlorobenzothiazole (XIV) yielded 42.6% 6-O2N derivative of XIV, m. 191-3° (nitration at 30-5° increased the yield to 75%); 5 g. of the nitrated product, m. 102-15°, of I, 60 ml. concentrated HCl, and 18 g. SnCl2.2H2O heated 1 hr. on a water bath gave the NH2 derivatives which were dissolved in 7 ml. 18% HCl, diazotized with 0.92 g. NaNO2 in 1 ml. water, and the diazo compound converted into the Cl derivative gave 1.5 g. 6-Cl derivative (XVI) of I (picrate, m. 132-4°) (141°, recrystallized from EtOH); nitration of V at 0° and 30-5° yielded 28 and 45%, resp., of 6-O2N derivative (XVII) of V, m. 187°; nitration of XI at 0-2° yielded 72% 6-O2N derivative, m. 165-6°, and 10% 2-hydroxy-6-nitrobenzothiazole (XVIII), m. 226°; no nitration product was obtained from 2-nitrobenzothiazole.
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