With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.15864-32-1,2-Amino-6-bromobenzothiazole,as a common compound, the synthetic route is as follows.
Preparation Example 17; Preparation of Compound (17); Under argon atmosphere, 2-amino-6-bromobenzothiazole (20 g, 87.3 mmol) and 10 N KOH (100 mL) were added to ethylene glycol (20 mL), and the mixture was stirred at 125 C. under reflux for 15 hours. After cooling to room temperature, 12 N HCl (30 mL) was added to the reaction mixture to quench the reaction. The reaction mixture was then washed with water (100 mL) and extracted with EA (100 mL). Recrystallization from MeOH (200 mL) gave 2-amino-5-bromobenzenethiol (14 g, 68.6 mmol, 79%).In 1,4-dioxane (35 mL, 2.0 M), dissolved were 2-amino-5-bromobenzenethiol (14 g, 68.6 mmol) and salicylaldehyde (7.0 g, 57.2 mmol), and the solution was stirred at 100 C. under pressure for 12 hours. After cooling to room temperature, the reaction mixture was extracted with MC (150 mL), washed with water (100 mL) and dried under reduced pressure. Purification via silica gel column chromatography (n-hexane: MC=5:2) gave 2-(6-bromobenzo[d]thiazol-2-yl) phenol (15.5 g, 50.5 mmol, 88.3%).Under argon atmosphere, 2-(6-bromobenzo[d]thiazol-2-yl)phenol (15.5 g, 50.5 mmol) was dissolved in THF (160 mL, 0.3 M), and the solution was cooled to -78 C. To the solution, t-BuLi (1.7 M in hexane, 44.6 mL, 75.8 mmol) was added dropwise, and the mixture was stirred for 30 minutes. Triphenylsilyl chloride (TPSCl) (22.3 g, 75.8 mmol) dissolved in THF (50 mL) was slowly added thereto. The reaction mixture was stirred for 12 hours while slowly raising the temperature to room temperature. After quenching the reaction by adding water (100 mL), the reaction mixture was extracted with MC (80 mL). Drying under reduced pressure and purification via silica gel column chromatography (n-hexane: MC=3:1) gave 2-(6-triphenylsilylbenzo[d]thiazol-2-yl)phenol (20.4 g, 42 mmol, 83%).Compound (17) (1.0 g, 0.72 mmol, 45%) was obtained by repeating the same procedure as described in Preparation Example 1, but using 2-(6-triphenylsilylbenzo[d]thiazol-2-yl)phenol (2.0 g, 4.1 mmol), ZnCl2 (375 mg, 2.7 mmol), EtOH (70 mL, 0.02 M), NH4OH (2.0 mL) and water (20 mL).mp. >300 C.1H NMR (300 MHz, CDCl3): d=8.40-8.34 (m, 2H), 7.83-7.55 (m, 7H), 7.35 (s, 9H), 7.31 (d, J=5.1 Hz, 1H), 7.0-6.7 (m, 3H)MS/FAB: 1580.22 (found), 1584.77 (calculated), 15864-32-1
The synthetic route of 15864-32-1 has been constantly updated, and we look forward to future research findings.
Reference：
Patent; Gracel Display Inc.; US2010/152455; (2010); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica