2-Chloro-6-cyanobenzothiazole

Step A: 2-Chlorobenzothiazole-6-carbonitrile; To a mixture of 4-aminobenzonitrile (23.6 g, 0.2 mol) and ammonium rhodanate (30.4 g, 0.4 mol) was added glacial acetic acid (600 ml.) and the resulting solution was cooled to 13.5 To a solution of CuC1 (0.13 g, 1.02 mmol) in MeCN (4 ml) was added tert butyl nitrite (0.24g, 2.00 mmol) at 0°C. The reaction mixture was stirred at 0°C for 10 mm and then treated with 2-aminobenzo[djthiazole-6-carbonitnle (0.18 g, 1.02 mmol). The reaction mixture was heated at 70°Cfor 1 h. The resulting reaction mixture was poured into water (50 ml) and extracted with EtOAc (3 x15 ml). The combined organic phase was dried over Na2SO4, filtered and concentrated under reducedpressure. The residue was tnturated with n-pentane (2 x 5 ml) yielding 2-chloro-benzo[djthiazole-6- carbonitrile (0.165 g, 0.84 mmol). This material was directly used in the next step without further purification. LCMS: Method C, 2.27 mi MS: ES+ 195; ‘H NMR (400 MHz, DMSO-d6) ppm 8.70 (s, 1 H), 8.15 (d, J8.40 Hz, 1 H), 7.98 (d, J8.40 Hz, 1 H).General procedure: A mixture of the 2-mercaptobenzo[d]thiazole (>1 g, 1 equiv) and sul-furyl chloride (10 equiv) was stirred at 20–25 °C for 15 min. Next, H 2 O(2 equiv) was added and the mixture was stirred at 20–25 °C for anadditional 3 h. A sample was taken, quenched with MeCN/H 2 O (2:1)and analyzed by HPLC. After completion of the reaction, the mixturewas diluted with MeCN (5 volumes) and slowly quenched with H 2 O(20 volumes). The product precipitated from the aqueous solution.The solid was collected and washed with H 2 O. Drying under vacuumafforded the pure product. In the case of the liquid product 2-chloro-benzo[d]thiazole (13), the reaction mixture was extracted withEtOAc. The organic layer was then dried and concentrated to affordthe product as an oil.The mixture of compound HY (2.1 g, 10.93 mmol) in SO

Molecular Weight:194.64
XLogP3:3.3
Hydrogen Bond Acceptor Count:3
Exact Mass:193.9705470
Monoisotopic Mass:193.9705470
Topological Polar Surface Area:64.9
Heavy Atom Count:12
Complexity:224
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes