Sulfuric Acid → HCID 11673059, compound

Participants

Reaction Steps

N-benzyl-S-(naphthoquinon-2-yl)-dithiocarbamate) (32). To a suspension of benzylamine hydrochloride (300 mg, 1.87 mmoles) in CH2Cl2 (5 mL) at 0° C. was added NEt3 (208.4 mg, 2.05 mmoles) and the reaction mixture was stirred for 15 minutes followed by the addition of CS2 (142.5 mg, 1.87 mmoles). After 30 minutes, 1,4-naphthoquinone (296.1 mg, 1.87 mmoles) was added and the reaction was allowed to slowly warm to rt overnight. The reaction was poured into 1 M H2SO4 and extracted with EtOAc (3×50 mL). The organic layer was washed with brine, dried with Na2SO4, and filtered. Concentration afforded a crude product that was chromatographed (CHCl3/EtOAc/Hexanes, 1:1:2) to afford a brick red solid (125 mg, 20% yield).

Provenance & Evidence