Water → N-[5-fluoro-1-(o-methoxyphenyl)-1H-benzotriazol-6-yl]-1-cyclohexene-1,2-dicarboximide

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Reaction Steps

A solution of 6-amino-5-fluoro-1-(o-methoxyphenyl)-1H-benzotriazole (5.10 g, 0.019 mol) and 3,4,5,6-tetrahydrophthalic anhydride (3.68 g, 0.024 mol) in acetic acid is refluxed for 6 hours, cooled to room temperature and poured into water. The resultant aqueous mixture is extracted with ethyl acetate. The organic extracts are combined, washed sequentially with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain an orange oil. Flash column chromatography of the oil using silica gel and 2.5% to 5% ethyl acetate in methylene chloride solutions gives the title product as an orange solid, mp 83°-87° C.

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