Tetrahydrofuran → 5-Isothiocyanato-6-methoxy-2-(pyridin-3-yl)-1,3-benzothiazole

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Reaction Steps

5-Amino-6-methoxy-2-(2-pyridinyl)benzothiazole, 8.3 g, 0.0325 mole, is dissolved in 400 cc of tetrahydrofuran containing 9.5 cc, 0.065 mole of triethylamine. Thiophosgene, 2.5 cc, 0.0325 mole, is added, and the resulting mixture stirred at ambient temperature for 4 hours. The precipitate which forms is filtered and washed with tetrahydrofuran. The filtrate is concentrated to dryness. The residue is adsorbed on a silica gel column and eluted with hexane-ethylacetate to yield 1.8 g of crude product. Recrystallization from MeCN/CHCl3 yields 1.2 g of the title product, m.p. 164°-166°.

Provenance & Evidence