Triethylamine → 5-Isothiocyanato-2-(pyridin-3-yl)-1,3-benzothiazole

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Reaction Steps

5-Amino-2-(3-pyridinyl)benzothiazole, 8.0 g, 0.035 M, is dissolved in 400 cc of tetrahydrofuran and 9.8 cc, 0.070 M, of triethylamine. Thiophosgene, 2.7 cc, 0.035 M is added, and the resulting mixture stirred overnight at ambient temperature. The solids which form are filtered and washed with tetrahydrofuran. The filtrate is concentrated to dryness and chromatographed on Alumina IV; elution with benzene yields 1.0 g of white solid which is recrystallized from acetonitrile to yield the title compound, 0.52 g, m.p. 160°-162° (12% of theory).

Provenance & Evidence