ChemicalBook CAS DataBase List 4-Benzothiazolol

4-Benzothiazolol synthesis

6synthesis methods

Product Name:4-Benzothiazolol
CAS Number:7405-23-4
Molecular formula:C7H5NOS
Molecular Weight:151.19

3048-46-2
48 suppliers
$150.00/250mg

7405-23-4
101 suppliers
$23.00/100mg

Yield: 80%

Reaction Conditions:

with boron tribromide in 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; pH=7 at 40;

Steps:

4-Hydroxy-benzothiazole
4-Hydroxy-benzothiazole Boron bromide (3. 09ML, 1M solution in DCM, 3.09 mmol) was added dropwise at 0 C to a stirred solution OF 4-METHOXY-BENZOTHIAZOLE (510 mg, 3.09 mmol) in dry DCM (30ML). The resulting solution was warmed to 40 C and allowed to stir overnight. The resulting solution was concentrated IIZ vacuo and diluted with water and HCl (2N). The aqueous phase was neutralised to pH-7 with NaHC03 and the solution extracted with EtOAc (3 x 100 ml) and the combined organic extracts dried (MGS04) and the solvent removed III vacuo. The resulting oil was purified by flash chromatography eluting silica gel with hexane: EtOAc [4: 1] to hexane: EtOAc [7: 3] to give the title compound as a tan solid (730mg, 80%) ; ON (300 MHz, CDC13) 7.59 (1H, s, C$, 7.46 (1H, dd, Ar), 7.36 (1H, t, Ar), 7.02 (1H, dd, Ar).

References:

ELI LILLY AND COMPANY WO2004/43903, 2004, A1 Location in patent:Page 68 - 69