Isopropanol → 2,5-Dichloro-4-(2-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]ethenyl)-nitrobenzene

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Reaction Steps

2,5-Dichloro-4-(2-dimethylaminoethenyl)-nitrobenzene (15 g, 0.057 mol) and 4-(1,2-benzisothiazol-3-yl)-piperazine (18.9 g, 0.086 mol) were combined in acetic acid (150 ml) and stirred overnight at room temperature under a nitrogen atmosphere. The slurry was poured slowly into a mixture of hexanes (300 ml) and isopropanol (300 ml) with stirring. The product was isolated by filtration as a brick red solid and washed with hexanes. The yield was 23.4 g, 93%; mp 194°-5° C. NMR (CDCl3) δ 8.05 (s, 1), 7.95-7.80 (m, 2), 7.56-7.35 (m, 3), 7.01 (d, 1), 5.60 (d, 1), 3.95-3.46 (m, 8). Analysis Calculated for C19H16N4O2Cl2S: C, 52.41; H, 3.70; N, 12.87. Found: C, 52.05; H, 3.36; N, 12.58.

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