Water → HCID 19385238, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-methoxy-5-methylbenzo[d]thiazol-2-amine (5A) (1.24 g, 6.42 mmol) in H3PO4 (5 mL) at 0° C., was added NaNO2 (2.2 g, 32 mmol) in minimal amount of water. The reaction mixture was stirred at 0° C. for 20 min. The reaction mixture was then transferred to ice-cold hypophosphorous acid (50%, 5 ml) and slowly warmed to room temperature and stirred at room temperature until gas evolution ceases. Solid Na2CO3 was added to neutralize the reaction and the mixture was extracted by ethyl acetate. The organic phase was dried over MgSO4, filtered, concentrated and purified by silica gel column (0-100% ethyl acetate/hexanes). LCMS-ESI+: calc'd for C9H9NOS: 180.0 (M+H+). Found: 180.1 (M+H+).

Provenance & Evidence