A one-pot strategy for the synthesis of 2-aminobenzothiazole in water by copper catalysis was written by Khatun, Nilufa;Jamir, Latonglila;Ganesh, Majji;Patel, Bhisma K.. And the article was included in RSC Advances in 2012.Quality Control of N-Phenylbenzo[d]thiazol-2-amine This article mentions the following:
A straightforward, efficient and sustainable method (green chem.) for the synthesis of 2-aminobenzothiazole derivatives has been achieved from in-situ generated 2-halo thioureas using a copper(I) catalyst in water as a reaction medium. The present study demonstrates that copper iodide (CuI) exhibits better efficiency in water towards intramol. S-arylation compared to other organic solvents. While (2-iodoaryl)thioureas are smoothly converted to the desired product in high yield with only a catalytic quantity of CuI, addition of base and ligand are essential for bromo analogs and chloro analogs. The title compounds thus formed included N-(2-methoxyphenyl)-2-benzothiazolamine (I) [N-(2-methoxyphenyl)-6-methyl-2-benzotiazolamine]. An unprecedented demethoxylation of a (2-methoxyphenyl)thiourea intermediate followed by a Friedel-Crafts type methylation (para to nitrogen) was observed in the aryl ring possessing the original methoxy group and the product thus formed was N-(2-iodo-4-methylphenyl)-6-methyl-2-benzotiazolamine (II). The synthesis of the target compounds was also achieved by a reaction of 1-iodo-2-(isothiocyanato)benzene with morpholine, piperidine, pyrrolidine and the products thus formed included 2-(4-morpholinyl)benzothiazole, 2-(1-piperidinyl)benzothiazole and 2-(1-pyrrolidinyl)benzothiazole. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Quality Control of N-Phenylbenzo[d]thiazol-2-amine).
N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) belongs to thiazole derivatives. Thiazole is a five-membered, unsaturated, planar, π-excessive heteroaromatic containing one sulfur atom and one pyridine-type nitrogen atom at position 3 of the cyclic ring system. There are numerous natural products that possess a thiazole ring with broad pharmacological activities. Thiamine, also known as vitamin B1, possesses a thiazole ring linked with 2-methylpyrimidine-4-amine as hydrochloride salt.Quality Control of N-Phenylbenzo[d]thiazol-2-amine
Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica