6-CHLORO-3H-BENZOTHIAZOL-2-ONE

White solid

6-Chloro-2(3H)-benzothiazolone 4.081 gm (0.02 mol) of 2, 6-dichloro-benzothiazole were refluxed for 4 hours in 100 ml of a mixture of equal parts of ethanol and concentrated hydrochloric acid. After distilling the reaction mixture with 100 ml of water, the resulting precipitate was filtered off and washed thoroughly with water. For further purification the precipitate was taken up in aqueous 10% sodium hydroxide, the solution was filtered, and the filtrate was extracted twice with 100 ml each of ether. The aqueous phase was acidified with hydrochloric acid, and the resulting precipitate was collected by suction filtration, washed with water and recrystallized once from ethanol and once from toluene, each time in the presence of activated charcoal. 3.1 gm (83% of theory) of crystals with a melting point of 212-213 C. were obtained. According to mixed melting point determination, elemental analysis, and thin-layer chromatography, the product was identical to the product obtained in Example 6.EXAMPLE 8 6-Chloro-2(3H)-benzothiazolone 4.081 gm (0.02 mol) of 2, 6-dichloro-benzothiazole were refluxed for 4 hours in 100 ml of a mixture of equal parts of ethanol and concentrated hydrochloric acid. After distilling the reaction mixture with 100 ml of water, the resulting precipitate was filtered off and washed thoroughly with water. For further purification the precipitate was taken up in aqueous 10% sodium hydroxide, the solution was filtered, and the filtrate was extracted twice with 100 ml each of ether. The aqueous phase was acidified with hydrochloric acid, and the resulting precipitate was collected by suction filtration, washed with water and recrystallized once from ethanol and once from toluene, each time in the presence of activated charcoal. 3.1 gm (83% of theory) of crystals with a melting point of 212-213 C. were obtained. According to mixed melting point determination, elemental analysis, and thin-layer chromatography, the product was identical to the product obtained in Example 6.General procedure: A Schlenk tube was charged with ethyl 2-iodo-phenylcarbamates (1 mmol), CuI (19mg, 0.1 mmol), and Na2S*9H2O (3 mmol). The tube was evacuated and backfilled with argon (3 times), and the 2 mL of DMF was added. The reaction mixture wasstirred at 80 C for 10-16 h, then 3 mL of AcOH was added to the cooled reaction mixture and the mixture was stirred at 130 C for another 36 h. Saturated NaHCO3 (10mL) was added and the mixture was extracted with ethyl acetate. The organic layer was washed with H2O, brine, and dried over Na2SO4. After removal of the solvent in vacuo, the residue was purified by column chromatography on silica gel to provide the desired benzothiazolone.

Molecular Weight:185.63
XLogP3:2.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:184.9702126
Monoisotopic Mass:184.9702126
Topological Polar Surface Area:54.4
Heavy Atom Count:11
Complexity:187
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes