2-Benzothiazolamine,7-nitro-(9CI)

Step 3: 7-nitrobenzo[d]thiazol-2-amine[244] To a stirred solution of 1-(3-nitrophenyl)thiourea (5.16 g, 26.20 mmol) prepared in Step 2 in chloroform (130 mL) was added dropwise bromine (2.68 mL, 52.3 mmol) at room temperature. The reaction mixture was refluxed for 3 hours and then cooled to room temperature. The reaction mixture was diluted with isopropyl ether and then filtered. The resuting solid was dissolved in water and then basified to pH 11-12 with sodium carbonate. The aqueous layer was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and then filtered. The filtrate was concentrated under reduced pressure. The resulting solid was dried under reduced pressure to give 3.52 g of the titled compound as a yellow solid (Yield: 69percent). [245] Step 3: To 0.60 g (3.0 mmol) of (3-nitrophenyl) thiourea in 25 mL of carbon tetrachloride was added 0.17 mL (3.4 mmol) of bromine in 10 mL of carbon tetrachloride dropwise over 1 h. The mixture was heated to reflux for 18 h, cooled to room temperature and the precipitate that formed was collected by filtration. The precipitate was slurried in glacial acetic acid and the solids were collected by filtration. The solids thus obtained were slurried in water and saturated potassium carbonate was added until the pH was about 9. The free base was collected by filtration to give 0.30 g (51percent) of the title compound as a light orange solid. MS Calcd.: 195 ; Found: 196 (M+H).

Molecular Weight:195.20
XLogP3:1.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Exact Mass:195.01024758
Monoisotopic Mass:195.01024758
Topological Polar Surface Area:113
Heavy Atom Count:13
Complexity:220
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes