Carbon Disulfide → HCID 86623878, compound

Participants

Reaction Steps

To a solution of 1,2-diamino-3,4,5-trifluoro-benzene (2.5 g, 15.4 mmol) in 20 mL of tetrahydrofuran under argon, are added 2.3 mL (38.6 mmol) of carbon disulfide. The reaction mixture is heated at reflux temperature for 3 h, upon which 2.3 mL (38.6 mmol) of carbon disulfide are added and reflux is maintained for 16 h. Carbon disulfide 2.3 mL (38.6 mmol) is added and reflux is maintained for 8 h, upon which 2.3 mL (38.6 mmol) of carbon disulfide are added and reflux is maintained for 16 h. The reaction mixture is then cooled to room temperature and concentrated to dryness under reduced pressure. The residue is purified by chromatography on a prepacked 90 g 15-40 μm silica gel cartridge (eluting solvent: cyclohexane/ethyl acetate 90/10 v/v; rate: 35 mL/min). The fractions containing the desired product are combined and concentrated to dryness under reduced pressure. The residue is purified by chromatography on a prepacked 90 g 15-40 μm silica gel cartridge (eluting solvent: dichloromethane/methanol 100/0, then 98/2 v/v; rate: 40 mL/min). The fractions containing the desired product are combined and concentrated to dryness under reduced pressure. 0.72 g of 4,5,6-trifluoro-1,3-dihydro-benzimidazole-2-thione is obtained as an off-white solid. LCMS-DAD-ELSD: 203(−): [M−H]−; 205(+): [M+H]+.

Provenance & Evidence