Hydrochloric Acid → (3S)-3-Hydroxymethyl-1,2,3,4-tetrahydro-beta-carboline-2-carbodithioic acid

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Reaction Steps

(3S)-3-Hydroxymethyl-1,2,3,4-tetrahydro-β-carboline (2.02 g) is dissolved in dimethylsulfoxide (10 ml), and thereto are added triethylamine (1.67 ml) and CS2 (0.72 ml), and the mixture is stirred at room temperature for 3 hours. The reaction mixture is poured onto ice-water and is neutralized with 10% HCl. The precipitated crystals are collected by filtration, washed with water and then recrystallized from methanol to give the title compound (1.46 g, 60%) as colorless needles, m.p. 225°-227° C. IR νmaxNujol (cm-1): 3480, 3340; Mass m/e: 278 (M+), 244 (M+ --H2S); [α]D20 +170.0° (c=1.0, methanol).

Provenance & Evidence