反应详情

4-hydroxybenzoic acid hydrazide (3.0 g, 19.66 mmol) and S-methyl N-[4-chloro-3-(trifluoromethyl)phenyl]isothiourea hydroiodide (7.8 g, 19.66 mmol) were suspended in 100 mL of anhydrous pyridine. The reaction mixture was refluxed for 18 hours under Ar atmosphere. Then it was cooled down to ambient temperature and pyridine was removed in vacuo. The resulting yellow oil was re-dissolved in a small amount of ethyl acetate, loaded on a short pad of silica gel and eluted with 5:1 hexane/ethyl acetate, then with 100% ethyl acetate to collect the product. The product was re-purified by a second silica gel column chromatography, using ISCO system (80 g pre-packed column, 25 min run, 20% to 50% EtOAc gradient in hexane). Solvent was removed in vacuo to give the title product as a white solid (2.83 g). Yield 40.4%.

1. temperatureThe reaction mixture was refluxed for 18 hours under Ar atmosphere
2. custompyridine was removed in vacuo
3. dissolutionThe resulting yellow oil was re-dissolved in a small amount of ethyl acetate
4. washeluted with 5:1 hexane/ethyl acetate
5. customwith 100% ethyl acetate to collect the product
6. customThe product was re-purified by a second silica gel column chromatography
7. customISCO system (80 g pre-packed column, 25 min run, 20% to 50% EtOAc gradient in hexane)
8. customSolvent was removed in vacuo