Hydrochloric Acid → HCID 178427887, compound

Participants

Reaction Conditions

Reaction Steps

3,4-Difluoro-2-(4-iodo-2-methyl-phenylamino)-benzoic acid hydrazide (170 mg, 0.42 mmol) was suspended in 7 mL of absolute EtOH and cooled to 0° C. Carbon disulfide (74 mg, 0.97 mmol) was added followed by 24 mg (0.42 mmol) of powdered KOH. The reaction was stirred for 1 h at 0° C., 1 h at rt, and refluxed for 3 h to afford a homogeneous reaction. The reaction was cooled to rt. at which point a ppt formed. Water was added and the reaction diluted with 5 mL of EtOAc. 1N HCl was added to acidify the aqueous layer (pH=2). The aqueous layer was extracted with EtOAc (3×). The combined organic layers were dried over Na2SO4 and concentrated to obtain 96 mg (51%) of 5-[3,4-Difluoro-2-(4-iodo-2-methyl-phenylamino)-phenyl]-[1,3,4]oxadiazole-2-thiol as a yellow powder. M.p.=231.8-232.8° C. 1H NMR (400 MHz, CDCl3) δ7.62 (m, 2H), 7.47 (s, 1H), 7.30 (complex m, 2H), 6.44 (dd, J=8.0, 4.5 Hz, 1H), 2.19 (s, 3H).

Provenance & Evidence