3-Methoxy-4-nitrobenzoic acid → 2-(3-Methoxy-4-nitrophenyl)-6-methoxybenzothiazole

Participants

Reaction Conditions

Reaction Steps

A thoroughly mixed paste of 2-amino-5-methoxybenzenethiol (2.0 g, 12.88 mmol) and 3-methoxy-4-nitrobenzoic acid (2.54 g, 12.88 mmol) in trimethylsilylpolyphosphate (10 ml) was stirred and heated at 150° C. under an atmosphere of argon for 2 h. On cooling to room temperature, the reaction mixture was suspended in DCM (300 ml) and adsorbed onto flash silica and initially purified using a plug of flash silica eluting with DCM, then DCM/EtOAc (6:1). Further purification of the collected fractions by flash chromatography (20:1 DCM/Hexane) gave the title compound (1.32 g, 32%) as a yellow solid.

Provenance & Evidence