Action of chlorine on aryl thiocarbimides and the reactions of aryl isocyanodichlorides was written by Dyson, G. Malcolm;Harrington, Thomas. And the article was included in Journal of the Chemical Society in 1940.Recommanded Product: 1843-21-6 This article mentions the following:
PhNCS (20 g.) in 64 g. CHCl3, treated with Cl without cooling until the increase in weight is 2 g., gives bis(phenylthiocarbimide) oxide, yellow, m. 118°; p-tolyl analog, m. 139°; m-isomer, m. 128°; p-bromophenyl analog; no oxides were obtained from o-MeC6H4NCS or from o-, m- and p-O2NC6H4NCS. PhNCS (20 g.) in 10 g. CHCl3, treated with Cl until the increase in weight is 7 g., gives 1-anilinobenzothiazole (I), m. 159° (picrate, yellow, m. 221°). CS(NHPh)2 and Br in CHCl3, boiled 0.5 h., give red needles of a Br addition product; reduction with SO2 in H2SO3 and treatment with hot 2 N NaOH give I. PhNCS (318 g.) in 289 g. PhN:CCl2 (II), treated with Cl with cooling for 8 h. (increase in weight of 363 g.) gives 256 g. of II, b. 209-11°, d15 1.285; the following isocyanodichlorides were prepared by treatment with Cl in 2-3 times their weight of CS2; they are colorless or pale yellow lachrymatory oils with unpleasant odors: p-bromophenyl, b15 122-4°, d15 1.5; p-anisyl, b15 155-60°, d15 1.5; p-tolyl, b20 121-4°, d15 1.2; m-tolyl, b10 130°, d15 1.35; o-tolyl, b15 125-30°, d15 1.3; m-nitrophenyl, prepared in warm CHCl3, pale yellow, b15 165-70°, m. 68°; m-isomer, m. 80°; the o-isomer could not be prepared II (5 g.) and 3.5 g. AcOH in 20 cc. C6H6, refluxed 2 h., give CO(NHPh)2 (III); the o- and p-tolyl analogs were similarly obtained; however, boiling 10 g. II with 25 cc. AcOH in 50 cc. C6H6 for 10 h. gives PhNHAc (IV); o-, m- and p-MeC6H4NHAc were similarly prepared Thus the reaction with AcOH proceeds as follows: 2II + 3AcOH → III + CO2 + HCl + 3AcCl; III + AcCl + AcOH → 2IV + CO2 + HCl. III is only very slowly hydrolyzed to IV by AcOH alone whereas in the presence of AcCl the reaction is rapid and proceeds to completion. The m-tolyl analog yields an unidentified N compound m. 278°. p-BrC6H4N:CCl2 and AcOH in C6H6 give (p-BrC6H4NH)2CO on refluxing 5 h. and p-BrC6H4NHAc on further boiling; m-O2NC6H4N:CCl2 behaves similarly. II, PhNH2 and C6H6, refluxed 5 h., give triphenylguanidine-HCl; analogs were prepared as follows, the m. p. of the HCl salt and the free base being given: phenyldi-p-tolyl 222-3°, 109°; m-isomer 206, 93°; o-isomer 205°, 100°; phenyldi-p-bromophenyl 257-62°, oil; p-tolyldiphenyl 230°, 128°; tri-p-tolyl 231°, 125°; p-tolyldi-p-bromophenyl 262-6°, 178°; tri-m-tolyl 221°, 107°; m-tolyldi-p-tolyl 218°, 105°; tri-o-tolyl 213-15°, 129°; o-tolyldi-p-tolyl 205-8°, 87°; tri-p-bromophenyl 270-6° (decomposition), 126°; p-bromophenyldi-p-tolyl 251°, 123°; m-nitrophenyldi-p-tolyl 201-5°, 179°; m-tolyl isomer 218-25°, 139°. The method constitutes a simple approach to the unsym. guanidines. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Recommanded Product: 1843-21-6).
N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) belongs to thiazole derivatives. Thiazole rings are planar and aromatic. Thiazoles are characterized by larger pi-electron delocalization than the corresponding oxazoles and have therefore greater aromaticity. 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.Recommanded Product: 1843-21-6
Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica