Extracurricular laboratory: Synthetic route of 116632-14-5

The synthetic route of 116632-14-5 has been constantly updated, and we look forward to future research findings.

116632-14-5, name is 3-Iodonaphthalen-2-amine, belongs to iodides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Application In Synthesis of 3-Iodonaphthalen-2-amine

Compound (3-1) (3-iodonaphtalen-2-amine, 1.00 g, 3.72 mmol), copper iodide (0.21 g, 1.11 mmol), potassium carbonate (1.02 g, 7.44 mmol), and dimethylsulfoxide (DMSO, 37 ml) are put in a reaction vessel, after argon gas is substituted for gas therein, and then, stirred. Subsequently, Compound (3-2) (benzoylthiocyanate, 1.81 g, 11.15 mmol) is added thereto, and the obtained mixture is stirred at 90 C. for 12 hours. The resultant is cooled down to room temperature, water is added thereto, the obtained mixture is cooled down to room temperature, and water is added thereto, an organic layer is extracted therefrom with ethyl acetate and dried with anhydrous sodium sulfate, and a solvent therein is distilled under a reduced pressure and removed. A residue therefrom is purified through silica gel column chromatography (hexane:ethyl acetate in a volume ratio of 5:1) to obtain Compound (3-3) (N-(naphtho[2,3-d]thiazol-2-yl)benzamide, 0.60 g). This solid is dissolved in methanol (35 ml). Then, 10 ml of a 2N sodium hydroxide aqueous solution is added thereto, and the obtained mixture is heated and stirred for one night. Subsequently, 100 ml of water is added thereto, and a solid precipitate therein is filtered and obtained. The solid is twice washed with water (30 ml) and dried to obtain Compound (3-4) (naphtho[2,3-d]thiazole-2-amine(naphtho[2,3-d]thiazol-2-amine, 0.26 g, a yield of 35%).

The synthetic route of 116632-14-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Samsung Electronics Co., Ltd.; Ishii, Norihito; Shibata, Katsunori; Ro, Takkyun; Kwon, Ohkyu; Kim, Sang Mo; Park, Kyung Bae; Yun, Sung Young; Leem, Dong-Seok; Lim, Youn Hee; Jin, Yong Wan; Choi, Yeong Suk; Choi, Jong Won; Choi, Taejin; Choi, Hyesung; Heo, Chul Joon; (50 pag.)US2019/51833; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com