6-Methyl-2(3H)-benzothiazolethione

General procedure: A sealed tube (50 mL) was charged with 2-haloaniline 1a (2mmol), CSTo the reaction tube was added 0.50 mmol (0.1435 g) of 2-iodo-4- (trifluoromethyl) aniline, 0.25 mmol (0.0600 g) of sodium hexahydrate, and then 2 mL of N, N-dimethylformamide and 1.50 mmo 1 (0.1142 g) of carbon disulfide, the reaction was stirred at 110 ° C for 12 hours. After TLC was tested, the reaction was complete. The reaction mixture was extracted with methylene chloride three times. The organic phases were combined and dried over anhydrous magnesium sulfate for 2 hours. The desiccant was removed by filtration and the residue was evaporated under reduced pressure to remove the dichloromethane solvent To obtain a crude product. The crude product was subjected to column chromatography (200-300 mesh silica gel) eluting with petroleum ether and ethyl acetate (8: 1-2: 1) to give purity of more than 99percent Of a white powder of 6-trifluoromethyl-2-mercaptobenzothiazole in a yield of 45.4percentGeneral procedure: A 25 mL reaction tube was charged with 2-haloaniline 1 (0.6 mmol), potassium o-ethyldithiocarbonate 2 (1.8 mmol), FeF3 (0.06 mmol), 2, 2’-bis(diphenylphosphino)-1, 1’-binaphthyl (0.03 mmol) and DMF (4 mL). The reaction vessel was flushed with argon for three times and sealed. Then the mixture was stirred electromagnetically in an oil bath at 110 for 3 - 21 hours. The reaction process was monitored by TLC on silica gel. After the reaction was completed, the reaction mixture was cooled to room temperature, then 4 mL HCl (3mol/L) was added and stirred for 30 minutes. Then the reaction mixture solution was extracted by ethyl acetate (3*20 mL). Subsequently, the combined organic solution were dried by anhydrous sodium sulfate and the target product was purified by silica gel colum chromatography (eluent: petroleum ether / ethylacetate) to give the corresponding pure product 3.General procedure: A 25 mL Wattecs reaction tube was charged with 2-haloaniline 1 (0.6 mmol), potassium O-ethyl dithiocarbonate 2 (1.8 mmol), CuCl (0.06 mmol), and DMF (2 mL). The reaction vessel was flushed with argon three times and sealed. Then the mixture was stirred electromagnetically in an oil bath at 110°C for 6 h.The reaction process was monitored by TLC on silica gel. After the reaction was completed, the reaction mixture was cooled to room temperature, and then HCl (3 mL, 3 mol/L) was added and stirred for another 30 min. The reaction mixture solution was extracted by ethyl acetate (3 × 20 mL). Subsequently, the combined organic solutions were dried by anhydrous sodium sulfate and the target product was purified by chromatography on a silica gel column (eluent: petroleum ether/ethyl acetate) togive the corresponding pure product 3. Complete characterization characterizationof the products (all known) is found in the Supplemental Materials (Figures S1–S13).General procedure: A round-bottomed flask was charged with 2-bromoaniline or 2-fluoro-aniline (>3 g, 1.0 equiv) and potassium O-ethyl carbonodithioate(1.5–1.7 equiv). The mixture was dissolved in DMF (10 volumes) andheated to 120–130 °C until the aniline was fully consumed (3–14 h).The reaction mixture was cooled to r.t. and filtered. The filtrate wasdiluted with H 2 O (50 volumes) and the pH was adjusted to 1–2 usingaqueous 2 M HCl. The solid precipitate was collected, washed withH 2 O and dried to yield the pure product.

Molecular Weight:181.3
XLogP3:2.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:181.00199157
Monoisotopic Mass:181.00199157
Topological Polar Surface Area:69.4
Heavy Atom Count:11
Complexity:181
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes