4,6-Dibromo-2-benzothiazolamine

White solid

To an ice-cooled mixture of 2, 4-dibromoaniline (25.0 g, 99.6 mmol), ammonium thiocyanate (30.5 g, 0.401 mol) in acetic acid (140 mL) was added dropwise a solution of bromine (10.2 mL, 0.199 mol) in acetic acid (25 mL) over 1 h. After stirring at room temperature for 2 h, the yellow insoluble material was collected by filtration. The yellow cake was suspended in water, and the pH was adjusted to 11 by adding potassium carbonate. The insoluble material was collected again, and the cake was purified by flash column chromatography on silica gel (Hexane:AcOEt = 3:1) to give the title compound as a yellow solid (8.12 g, 26percent). Mp 256–258 °C. To an ice-cooled mixture of To an ice-cooled mixture of 2, 4-dibromoaniline (25.0 g, 99.6 mmol), ammonium thiocyanate (30.5 g, 0.401 mol) in acetic acid (140 mL) was added dropwise a solution of bromine (10.2 mL, 0.199 mol) in acetic acid (25 mL) over 1 h. After stirring at room temperature for 2 h, the yellow insoluble material was collected by filtration. The yellow cake was suspended in water, and the pH was adjusted to 11 by adding potassium carbonate. The insoluble material was collected again, and the cake was purified by flash column chromatography on silica gel (Hexane:AcOEt = 3:1) to give the title compound as a yellow solid (8.12 g, 26percent). Mp 256'258 °C. 1H NMR (400 MHz, DMSO-d6) delta 7.59 (1H, d, J = 1.8 Hz), 7.92 (1H, d, J = 1.8 Hz), 7.97 (2H, s). 13C NMR (100 MHz, DMSO-d6) delta 110.6, 111.8, 122.9, 130.4, 133.1, 150.2, 167.6. IR (ATR) nmax 3452, 3270, 3061, 1633, 1526, 1426, 1313, 1267, 1109 cm-1. MS (FI) 305 (M+). HRMS (FI) calcd for C7H4Br2N2S (M+) 305.84619, found 305.84548.Listed below are some typical examples of said 2-aminobenzothiazole compounds:...2-amino-6-cyanobenzothiazole2-amino-6-thiocyanobenzothiazole2-amino-6-methylbenzothiazole2-amino-4, 6-dichlorobenzothiazole

Molecular Weight:308.00
XLogP3:3.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Exact Mass:307.84415
Monoisotopic Mass:305.84619
Topological Polar Surface Area:67.2
Heavy Atom Count:12
Complexity:181
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes