β-Anilinovinyl derivatives of heterocyclic bases. III. Synthesis and absorption spectra of new anilinovinyl derivatives was written by van Dormael, A. E.;Nys, J.. And the article was included in Bulletin des Societes Chimiques Belges in 1952.Synthetic Route of C13H10N2S This article mentions the following:
Compounds of type I were prepared by refluxing 0.01 mole I (R = H, X = I) with 0.02 mole of the aniline with the desired substituent 10 min. in 25 ml. EtOH, adding 15 ml. concentrated HCl, and refluxing a further 2 hrs.; cooling, dilution with 75 ml. H2O, filtering, and recrystallizing from alc. gave the following desired I [X–, R, m.p. (crystallization solvent), λmaximum (mμ), and log ε given]: I–, CO2H, 26-2° (EtOH), 423, 4.93; I–, CO2Et, 236-7° (EtOH), 425, 4.92; I–, Ac, 220-1° (aqueous EtOH), 429, 4.80; Cl–, NO2, 200-1° (PrOH), 442, 4.56. The I were considered to be analogous to the monomethine cyanine (II) of the ethiodide of benzothiazole (C.A. 36, 467.1) and to the substituted anils (III) of PhNHCH:CHCHO. Since the III series could not be made, a number of the dianils (IV) of glutaconaldehyde, [R’C6H4NHCH:CHCH:CHCH:NHC6H4R’-p]+X–, were prepared, the first 4 by the method of Zincke [via 1-(2,4-dinitrophenyl)pyridinium salts and ArNH2], the last 3 by the method of König (via 1-cyanopyridinium bromide and ArNH2) [R’, X, m.p., λmaximum (mμ) given]: H, Cl, 165-7° (from Me2CO by concentrated HCl, with repeated recrystallizations giving a lower m.p.), 485; Cl, Cl, 143° (MeOH), 494; MeO, Cl, 168-70° (3 EtOH crystallizations gave m. 127-9°), 509; Me2N, Cl, 164-6°, 548; CO2H, Cl, 177-9°, 498; CO2Et, Br, 175-8°, 506; Ac, Br, 174-6°, 513; NO2, Br, 149-50°, 524. λmaximum for III were calculated on the assumption that they were 102.5 mμ less than for IV (C.A. 36, 467.1; 43, 1653+). An average of λmaximum for II (423 mμ) and for III (calculated) was compared with λmaximum for I exptl., with good agreement (neg. deviation contrary to expectation); results compared with similar ones for unsym. substituted trimethinic cyanines (C.A. 40, 5922.7). In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Synthetic Route of C13H10N2S).
N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) belongs to thiazole derivatives. The thiazole ring has been identified as a central feature of numerous natural products, perhaps the most famous example of which is epothilone. The pyridine-type nitrogen in the thiazole ring deactivates the ring for electrophilic substitution reactions, which is further reduced in acid due to protonation of the thiazole ring.Synthetic Route of C13H10N2S
Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica