Sodium Hydroxide → HCID 402863, compound

Participants

Reaction Conditions

Reaction Steps

5-Fluoro-2-(4′-amino-3′-cyanophenyl)benzothiazole (1 g, 3.75 mmol) was dissolved in 80% sulfuric acid (50 ml) and heated at 100° C. for 2 hrs. After cooling, the reaction mixture was diluted with water (100 ml) and the pH adjusted to 7.5 using 50% sodium hydroxide. The product was extracted with ethyl acetate(3×50 ml), the extracts dried (Na2SO4) and evaporated to leave a yellow solid which was taken up in THF (20 ml) and added dropwise to a solution of LiAlH4 (0.7 g, 0.019 mol) in THF (15 ml). After stirring at 25° C. for 2 hrs, water (20 ml) was added and the product extracted with ethyl acetate (3×50 ml). The organic extracts were washed with brine (10 ml), dried (Na2SO4) and evaporated. The residue was purified by column chromatography (10% ethyl acetate/dichloromethane) to leave a yellow powder.

Provenance & Evidence