6-Chloro-2-methylbenzothiazole

Yellow solid

Step (iii): 6-Chloro-2-methyl-l, 3-benzothiazole To a suspension of sodium hydride (2.88 g, 120.21 mmol) in anhydrous toluene (500 ml) was added N-(4-chloro-2-fluorophenyl)ethane thioamide (20.0 g, 109.28 mmol) in one portion at 0 C. The resulting solution was allowed to warm to room temperature over 1 hour and then heated to reflux. After 30 min, DMF (60 ml) was carefully added and the reaction was stirred for an additional 2 hours. The mixture was then cooled to 0 C and added to ice-water before being extracted with ethyl acetate. The combined organics were washed with brine and dried (magnesium sulphate) filtered and concentrated in vacuo to afford the title compound. 1H NMR (DMSO-d6) delta ppm 2.79 (s, 3 H), 7.49-7.51 (d, 1 H) 7.88-7.91 (d, 1 H), 8.17 (s, 1 H)General procedure: 2-methylbenzo[d]thiazole (13a, 745mg, 5mmol) was refluxed with selenium dioxide (2775mg, 25mmol) in dioxane for 12h. After completion of the reaction the black solid of Selenium was filtered off on celite and the dioxane was removed under reduced pressure. Water was added to the reaction mixture and the compound was extracted using ethyl acetate. The compound was further purified using column chromatography on silica gel 60-120 mesh to afford the pure solid in moderate yield (52%).

Molecular Weight:183.66
XLogP3:3.4
Hydrogen Bond Acceptor Count:2
Exact Mass:182.9909481
Monoisotopic Mass:182.9909481
Topological Polar Surface Area:41.1
Heavy Atom Count:11
Complexity:153
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes