7-Bromo-6-benzothiazolamine

To a solution of benzo[d]thiazol-6-amine (100 mg, 0.67mmol) in 6 ml CHClA mixture of benzo[djthiazol-6-amine (2-17, 1 g, 6.6 mmol) and Br2 (1.06 g, 6.6 mmol) in CHC13 (5 mL) was stirred at 0 °C for 1 h. Upon reaction completion, the resulting mixture was concentrated under reduced pressure to provide intermediate 2-18 (yellow solid, 1.2 g, 75percent yield). LCMS (m/z): 229 [M + HI .Step A: 7-bromo-benzothiazol-6-ylamineTo a solution of benzothiazol-6-ylamine (6.4 g, 42.6 mmol) in glacial acetic acid (40 mL) was added bromine (2.18 mL) in glacial acetic acid (10 mL) dropwise. The reaction mixture was stirred at RT for 1 h. Water (160 mL) was added to the reaction mixture and the solid formed was extracted with ethyl acetate (3 x 40 mL). The combined organic fractions were washed with saturated aqueous sodium bicarbonate solution (200 mL), water (100 mL), and brine (20 mL), dried over anhydrous sodium sulfate, and concentrated. Purification of the residue by column chromatography (20percent ethyl acetate: hexanes) afforded 6.5 g (67percent) of the title compound as a yellow solid. 7-Bromo-6-aminobenzothiazole To a solution of benzo[d]thiazol-6-amine (100 mg, 0.67mmol) in 6 ml CHCl3 was added Br2 (42 mg, 0.27mmol) in CHCI3 (10ml) dropwise about 15 min. The mixture was concentrated under reduced pressure, and the residue was crystallized from DCM:MeOH (5: 1) to give 7-bromobenzo[d]thiazol-6-amine (80mg, 80%).A mixture of benzo[djthiazol-6-amine (2-17, 1 g, 6.6 mmol) and Br2 (1.06 g, 6.6 mmol) in CHC13 (5 mL) was stirred at 0 C for 1 h. Upon reaction completion, the resulting mixture was concentrated under reduced pressure to provide intermediate 2-18 (yellow solid, 1.2 g, 75% yield). LCMS (m/z): 229 [M + HI .Step A: 7-bromo-benzothiazol-6-ylamineTo a solution of benzothiazol-6-ylamine (6.4 g, 42.6 mmol) in glacial acetic acid (40 mL) was added bromine (2.18 mL) in glacial acetic acid (10 mL) dropwise. The reaction mixture was stirred at RT for 1 h. Water (160 mL) was added to the reaction mixture and the solid formed was extracted with ethyl acetate (3 x 40 mL). The combined organic fractions were washed with saturated aqueous sodium bicarbonate solution (200 mL), water (100 mL), and brine (20 mL), dried over anhydrous sodium sulfate, and concentrated. Purification of the residue by column chromatography (20% ethyl acetate: hexanes) afforded 6.5 g (67%) of the title compound as a yellow solid. 1H NMR (300 MHz, CDCI3): delta 4.31 (br. s, 2H), 7.02 (d, J=8.4 Hz, 1 H), 7.92 (d, J=8.4 Hz, 1 H), 8.80 (s, 1 H).7-Bromo-6-aminobenzothiazole To a solution of 6-eminobenzothiazole (16 g, 107 mmol) in 100 mL of AcOH was added Br2 (2.0 mL, 43 mmol) dropwise and the resulting reaction mixture was stirred for 1 h at 25 C. Reaction mixture was concentrated in vacuo, yielding a yellow solid which was dissolved in EtOAc and washed with aq. NaHCO3. Organic layer was dried over Na2 SO4 and concentrated in vacuo, yielding an oil which was subjected to column chromatography (10-50% EtOAc/n-Hexane) to obtain 7.8 g (34 mmol, 80%) of the desired product.

Molecular Weight:229.10
XLogP3:2.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Exact Mass:227.93568
Monoisotopic Mass:227.93568
Topological Polar Surface Area:67.2
Heavy Atom Count:11
Complexity:155
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes