5-Benzothiazolemethanol(9CI)

To a mixture of compound B-187 (5.0 g, 26 mmol) in anhydrous tetrahydrofuran (50 mL) was added DIBAL-H (50 mL, 1 M in hexane) dropwise at -78 °C. The mixture was stirred at -78 °C for 2 hours. On completion, the reaction was quenched with water (50 mL) at 0 °C and filtered, and the filtrate was extracted with dichloromethane (3 x 100 mL). The combined organic layers were concentrated in vacuo to give compound B-188 (2.8 g, 65percent yield) as a yellow oil.To a mixture of compound B-188 (2.8 g, 17 mmol) in anhydrous dichloromethane (20 mL) was added manganese dioxide (14 g, 0.16 mol) at room temperature. The mixture was stirred at room temperature for 16 hours. On completion, the reaction was filtered, and the filtrate was concentrated in vacuo to give compound B-189 (2.5 g, 93% yield) as a yellow solid.To a mixture of compound B-187 (5.0 g, 26 mmol) in anhydrous tetrahydrofuran (50 mL) was added DIBAL-H (50 mL, 1 M in hexane) dropwise at -78 C. The mixture was stirred at -78 C for 2 hours. On completion, the reaction was quenched with water (50 mL) at 0 C and filtered, and the filtrate was extracted with dichloromethane (3 x 100 mL). The combined organic layers were concentrated in vacuo to give compound B-188 (2.8 g, 65% yield) as a yellow oil.(b) Benzothiazol-5-yl-methanol The acid (100 a) (0.53 g) in tetrahydrofuran (20 ml) and triethylamine (0.49 ml) was cooled to 0 C. and isobutylchloroformate (0.42 ml) was added dropwise and the solution was stirred at 0 C. for 1 hour, when it was filtered into a stirred solution of sodium borohydride (0.24 g) in ice/water (50 ml). The mixture was stirred at 0 C. for 0.5 hour, neutralised with 2M hydrochloric acid, evaporated to half volume, and extracted with dichloromethane. The organic fraction was dried, evaporated to dryness and chromatographed on silica gel (ethyl acetate) to give the alcohol (0.345 g) MS (+ve ion electrospray) m/z 166 (MH)+

Molecular Weight:165.21
XLogP3:1.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:165.02483502
Monoisotopic Mass:165.02483502
Topological Polar Surface Area:61.4
Heavy Atom Count:11
Complexity:142
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes