Carbon Disulfide → 5-(trifluoromethyl)-1,3-benzothiazole-2-thiol

Participants

Reaction Steps

Into a 25 ml round bottomed flask were added 2-amino-4-(trifluoromethyl)benzenethiol hydrochloride (107 mg, 0.43 mmol), CS2 (331 mg, 4.35 mmol), aqueous KOH (127 mg, 2.3 mmol), and EtOH (5 ml). The solution was refluxed under Ar for 2 h, cooled to rt, then treated with Amberlite IR-120(H+) (2 g, 3.8 mmol). The solution was filtered and concentrated to afford the title compound as a white crystalline solid (73.4 mg, 67%). 1H NMR (DMSO-d6) δ=7.46 (s, 1H), 7.61 (d, 1H), 7.93 (d, 1H), 13.99 (br s, 1H); ESIMS: m/z 234 (M−H).

Provenance & Evidence