6-BROMO-1,3-BENZOTHIAZOLE

Off-white powder

General procedure: A tube-type Schlenk flask was charged with 0.045 mmol of catalyst D, 0.045 mmol of 1, 8-diazabicyclo[5.4.0]undec-7-ene (7μL), and 1mL of N-methylpyrrolidone. The solution was stirred under nitrogen atmosphere at 60–70°C for 30 min. And, 2mL of N-methylpyrrolidone was added, followed by addition of a balloon charged with carbon dioxide gas. The solution was stirred at 60–70°C for 30 min. Then, 2-aminobenzenethiol derivatives (0.5 mmol), phenylsilane (1.5 mmol) dissolved in 0.5mL of N-methylpyrrolidone was added to the mixture. Reaction was carried out at 60–70°C for 18–30h. After the solution was cooled to room temperature, purification by flash chromatography on silica gel with n-hexane and ethyl acetate afforded benzothiazole derivatives.It was added in a closed reaction vessel 0.3mmol2-amino-6-bromo thiazole, 0.9mmol silver nitrite, 3mL1, 2-dichloroethane, the reaction mixture was stirred at the reaction condition of80 72 hours. After the reaction was stopped, cooled to room temperature, thereaction mixture was added 10mL diluted with dichloromethane, filtration andstripped of solvent under reduced pressure, the residue was purified by columnchromatography, eluent V (petroleum ether) / V (ethyl ester) = 6/1, to give6-chlorobenzothiazole, yield 79percent.Add anhydrous copper (II) bromide (1.79 g, 7.99 mmol), tert-butyl nitrite (1.2 mL, 9.98 mmol) and anhydrous acetonitrile (20 mL) to a round bottom flask fitted with a reflux condenser and an addition funnel. Heat at 65 C for 10 min. Add a solution of benzothiazol-6-ylamine (Lancaster; 1 g, 6.66 mmol) in acetonitrile (10 mL) over a period of 5 min via addition funnel. Stir at 65 C for 30 min. Cool to room temperature, pour into 20percent aqueous hydrochloric acid (100 mL), and extract with ether (2 x 100 mL). Wash the organic layer with 20percent aqueous hydrochloric acid. Dry the organic phase with sodium sulfate, filter, evaporate and chromatograph (10percent ethyl acetate/90percent hexanes) to give the title product (0.4 g, 29percent) as a pale yellow solid. MS (ESI) M/E 215 (M+1).[0408] A solution of sodium nitrite (0.147 g, 2.1 mmol) in water (1.0 mL) was slowly added to a suspension of 6-aminobenzothiazole (0.30 g, 2.0 mmol) in HBr (48percent in water, 3 mL) at 0 °C and then the mixture was stirred at roomtemperature for 30 min. The formed solution was then slowly added to a solution of copper (I) bromide (0.435 g, 3.0mmol) in HCl (conc., 5 mL) at 0 °C. After the addition, the mixture was stirred at 60 °C for 1.5 h. Cooled down, and thereaction mixture was basified with excess ammonia and extracted with diethyl ether. The combined extract was washedwith water, brine, dried and concentrated. The 6-bromobenzothiazole (0.26 g) was obtained by Combiflash and thenconverted to the final compound using procedures analogous to those for example 1, MS(ESI): (M+H)+ = 413.1

Molecular Weight:214.08
XLogP3:2.7
Hydrogen Bond Acceptor Count:2
Exact Mass:212.92478
Monoisotopic Mass:212.92478
Topological Polar Surface Area:41.1
Heavy Atom Count:10
Complexity:131
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes